Host material for delayed fluorescent materials, organic light-emitting device and compound

ABSTRACT

A compound represented by (Tr) n -Z is useful as a host material for delayed fluorescent materials. Tr represents a substituted or unsubstituted triphenylenyl group, and plural Tr&#39;s existing in the general formula (1) may be the same as or different from each other. Z represents a carbonyl group or a substituted or unsubstituted, n-valent aromatic hydrocarbon group. n represents an integer of 2 to 6, but when Z is a carbonyl group, n is 2.

TECHNICAL FIELD

The present invention relates to a compound useful as a host materialfor delayed fluorescent materials, and to an organic light-emittingdevice using the compound.

BACKGROUND ART

Studies are being actively performed for enhancing the light emissionefficiency of organic light-emitting devices such as an organicelectroluminescence devices (organic EL devices), etc. For example,regarding the light-emitting material for use in a light-emitting layer,development of delayed fluorescent materials is under way as those thatcan efficiently utilize the excitation energy thereof for lightemission. A delayed fluorescent material is a light-emitting materialthat radiates fluorescence directly from the excited singlet state andradiates fluorescence (delayed fluorescence) also from the excitedsinglet state formed through reverse intersystem crossing from theexcited triplet state, and the excited triplet state can also be made tocontribute toward fluorescence emission along with the excited singletstate. As an application of the delayed fluorescent material, there areseen some publications describing an organic electroluminescence devicehaving therein a light-emitting layer formed by a combination of adelayed fluorescent material and a host material.

For example, PTL 1 describes an example of producing an organic ELdevice having a light-emitting layer that contains1,3-bis(carbazol-9-yl)benzene (mCP) and a delayed fluorescent material.

PTL 2 describes an example of producing an organic EL device having alight-emitting layer that contains 4,4′-bis(N-carbazolyl)biphenyl (CBP)and a delayed fluorescent material.

CITATION LIST Patent Literature

PTL 1: JP-A 2013-253121

PTL 2: JP-A 2013-256490

SUMMARY OF INVENTION Technical Problem

As described above, PTL 1 describes formation of a light-emitting layerby combining a delayed fluorescent material and mCP, and PTL 2 describesformation of a light-emitting layer by combining a delayed fluorescentmaterial and CBP. Here, mCP and CBP employed in these publications haveheretofore been generally used as a host material for a fluorescentmaterial and a phosphorescent material. However, the present inventorshave actually investigated the organic EL devices having the hostmaterial as combined with a delayed fluorescent material, and have foundthat the device lifetime is only 50 hours or so and is short, and thedevices are impracticable. This is considered to be because a delayedfluorescent material differs from an ordinary fluorescent material orphosphorescent material in point of the light emission mechanism and, inaddition, a delayed fluorescent material greatly differs from anordinary light-emitting material in point of the characteristicsnecessary for host materials and the preferred structures of thematerials. However, there exists no literature that investigates thecharacteristics and the structures of host materials to be combined withdelayed fluorescent materials, and no one could expect what type ofcompound would be useful as a host material for delayed fluorescentmaterials, and the situation is such that no one could sufficientlyutilize the characteristics of delayed fluorescent materials.

Given the situation, the present inventors have made assiduous studiesof investigating the usefulness of various materials as a host materialfor delayed fluorescent materials. With that, the inventors have hit ona general formula of a compound useful as a host material for delayedfluorescent materials, and have further promoted assiduousinvestigations for generalizing the constitution of an organiclight-emitting device having a high light emission efficiency and a longdevice lifetime.

Solution to Problem

As a result of assiduous studies, the present inventors have found that,by using a compound having a structure where plural triphenylenyl groupsbond via a carbonyl group or an aromatic hydrocarbon group as a hostmaterial for delayed fluorescent materials, not only the device lifetimecan be more greatly prolonged than in the case of using a carbazole-typehost material but also high efficiency and low-voltage driving can beexpected. Based on these findings, the present inventors have nowreached providing the present invention as described below as a meansfor solving the above-mentioned problems.

[1] A host material for delayed fluorescent materials, containing acompound represented by the following general formula (1):

(Tr)_(n)-Z  General Formula (1)

[In the general formula (1), Tr represents a substituted orunsubstituted triphenylenyl group, and plural Tr's existing in thegeneral formula (1) may be the same as or different from each other. Zrepresents a carbonyl group or a substituted or unsubstituted, n-valentaromatic hydrocarbon group. n represents an integer of 2 to 6, but whenZ is a carbonyl group, n is 2.][2] The host material for delayed fluorescent materials according to[1], wherein Z is a substituted or unsubstituted, n-valent aromatichydrocarbon group.[3] The host material for delayed fluorescent materials according to[2], wherein Z is an n-valent benzene residue.[4] The host material for delayed fluorescent materials according to[3], wherein Tr bonds to at least the 1-position and the 3-position ofthe benzene residue.[5] The host material for delayed fluorescent materials according to[2], wherein Z is an n-valent biphenyl residue.[6] The host material for delayed fluorescent materials according to[2], wherein Z is an n-valent aromatic hydrocarbon group substitutedwith a substituted or unsubstituted alkyl group or a substituted orunsubstituted aryl group.[7] The host material for delayed fluorescent materials according to[1], wherein Z is a carbonyl group.[8] The host material for delayed fluorescent materials according to[7], wherein at least one Tr has a substituent represented by thefollowing general formula (2):

Tr⁴-CO—  General Formula (2)

[In the general formula (2), Tr⁴ represents a substituted orunsubstituted triphenylenyl group.][9] The host material for delayed fluorescent materials according to[8], wherein two Tr's have, in total, 1 to 5 substituents eachrepresented by the general formula (2).[10] The host material for delayed fluorescent materials according toany one of [7] to [9], which contains a partial structure with acarbonyl group bonding to the 2-position, the 3-position, the6-position, the 7-position, the 10-position or the 11-position of thetriphenylene ring inside the molecule.[11] The host material for delayed fluorescent materials according to[10], wherein all the carbonyl groups bonding to the triphenylene ringexisting inside the molecule bond to the 2-position, the 3-position, the6-position, the 7-position, the 10-position or the 11-position of thetriphenylene ring.[12] The host material for delayed fluorescent materials according toany one of [1] to [11], wherein at least one Tr in the general formula(1) is a triphenylenyl group substituted with a substituted orunsubstituted alkyl group or a substituted or unsubstituted aryl group.[13] An organic light-emitting device comprising a layer that containsthe host material of any one of [1] to [12] and a delayed fluorescentmaterial.[14] The organic light-emitting device according to [13], comprising alayer that contains the host material of any one of [1] to [12] and anyother host material other than that host material, and a delayedfluorescent material.[15] The organic light-emitting device according to [13] or [14], whichis an organic electroluminescence device.[16] A compound represented by the following general formula (3):

Tr¹-CO-Tr²  General Formula (3)

[In the general formula (3), Tr¹ and Tr² each independently represent asubstituted or unsubstituted triphenylenyl group, and Tr¹ and Tr² may bethe same as or different from each other.][17] A compound represented by the following general formula (4):

(Tr³)_(n1)-Z  General Formula (4)

[In the general formula (4), Tr³ represents a substituted orunsubstituted triphenylenyl group, and plural Tr³'s existing in thegeneral formula (4) may be the same as or different from each other. Z¹represents a substituted or unsubstituted n-valent aromatic hydrocarbongroup. n1 represents an integer of 2 to 6. At least one of Tr³ and Z¹ issubstituted with a substituted or unsubstituted alkyl group or asubstituted or unsubstituted aryl group. When Tr³ is unsubstituted, Z¹is a benzene ring residue substituted with a phenyl group or a methylgroup and bonds to Tr³ at least at the 1-position and the 3-position, oris a biphenyl residue substituted with a phenyl group.]

Advantageous Effects of Invention

The compound of the present invention is useful as a host material fordelayed fluorescent materials. In addition, the organic light-emittingdevice using the compound of the present invention as a host materialfor delayed fluorescent materials requires a low driving voltage andrealizes a high light emission efficiency, and has a long devicelifetime.

BRIEF DESCRIPTION OF DRAWINGS

FIG. 1 This is a schematic cross-sectional view showing an example of alayer configuration of an organic electroluminescence device.

FIG. 2 This is a graph showing the lifetime characteristics of theorganic electroluminescence device using the compound 1 of Example 1 andthe organic electroluminescence device using the comparative compound Aof Comparative Example 1.

FIG. 3 This is a graph showing the voltage-current densitycharacteristics of the organic electroluminescence device using thecompound 10 and CBP of Example 2, the organic electroluminescence deviceusing CBP of Comparative Example 2, and the organic electroluminescencedevice using the comparative compound B and CBP of Comparative Example3.

FIG. 4 This is a graph showing the current density-external quantumefficiency characteristics of the organic electroluminescence deviceusing the compound 10 and CBP of Example 2, the organicelectroluminescence device using CBP of Comparative Example 2, and theorganic electroluminescence device using the comparative compound B andCBP of Comparative Example 3.

FIG. 5 This is a graph showing the lifetime characteristics of theorganic electroluminescence device using the compound 10 and CBP ofExample 2 and the organic electroluminescence device using CBP ofComparative Example 2.

DESCRIPTION OF EMBODIMENTS

The contents of the present invention are described in detailhereinunder. The constitutional elements may be described below withreference to representative embodiments and specific examples of theinvention, but the invention is not limited to the embodiments and theexamples. In the description, a numerical range expressed with referenceto the expressions, an upper limit or less and/or a lower limit or more,means a range that includes the upper limit and/or the lower limit.

[Compound Represented by General Formula (1)]

The host material for delayed fluorescent materials of the presentinvention contains a compound represented by the following generalformula (1):

(Tr)_(n)-Z  General Formula (1)

In the general formula (1), Z represents a carbonyl group or asubstituted or unsubstituted, n-valent aromatic hydrocarbon group.

The aromatic ring of the aromatic hydrocarbon group that Z representsmay be a single-ring aromatic ring, or may be an aromatic ring of aring-assembly structure where two or more aromatic rings bond via asingle bond, such as a biphenyl ring, or may also be an aromatic ring ofa polycyclic condensed structure where two or more aromatic rings arecondensed such as naphthalene. Specifically, the aromatic hydrocarbongroup is preferably an aromatic hydrocarbon group having a ring skeletoncarbon number of 6 to 18. Preferably, the group is a residue of abenzene ring, a biphenyl ring, a naphthalene ring or a fluorene ring,more preferably a benzene residue or a biphenyl residue, and even morepreferably a benzene residue.

When Z is a carbonyl group, n is 2.

When Z is an aromatic hydrocarbon group, n is 2 to 6, preferably 2 to 3.The bonding position of Tr in the aromatic hydrocarbon group is notspecifically defined, but when Z is a benzene residue, preferably, Trbonds to at least the 1-position and the 3-position of the residue. Inthe methine group and the methylene group of the aromatic hydrocarbongroup to which Tr does not bond, the hydrogen atom may be substitutedwith a substituent, or may not be substituted. The substituent that maysubstitute in the aromatic hydrocarbon group includes those selectedfrom a group of the substituents to be mentioned hereinunder, and amongthese, a substituted or unsubstituted alkyl group or a substituted orunsubstituted aryl group is preferred. With that, the stability of thecompound represented by the general formula (1) may tend to increase.The alkyl group is preferably an alkyl group having 1 to 18 carbonatoms, and is more preferably a methyl group. For the description andthe preferred range of the aromatic ring that constitutes the arylgroup, the description and the preferred range of the aromatic ring ofthe aromatic hydrocarbon group that Z may represent may be referred to.Among these, the aryl group that may substitute in the aromatichydrocarbon group is preferably a biphenyl residue, or a benzene residue(a phenyl group), and is more preferably a phenyl group.

Tr represents a substituted or unsubstituted triphenylenyl group. Thebonding position of the triphenylenyl group to Z is not specificallydefined, but is preferably the 2-position. In the methine group of thetriphenylenyl group that does not bond to Z, the hydrogen atom may besubstituted with a substituent, or may not be substituted. Thesubstituting position in the case where the triphenylenyl group issubstituted with a substituent is preferably at least one of the6-position, the 7-position, the 10-position and the 11-position.

The substituent that may substitute in the triphenylenyl group includesthose selected from a group of the substituents to be mentionedhereinunder. Here, at least one Tr is preferably substituted with asubstituted or unsubstituted alkyl group or a substituted orunsubstituted aryl group. With that, the stability of the compoundrepresented by the general formula (1) may tend to increase. The alkylgroup is preferably an alkyl group having 1 to 18 carbon atoms, and ismore preferably a methyl group. For the description and the preferredrange of the aromatic ring that constitutes the aryl group, thedescription and the preferred range of the aromatic ring of the aromatichydrocarbon group that Z may represent may be referred to. Among these,the aryl group that may substitute in the triphenylenyl group ispreferably a biphenyl residue, or a benzene residue (a phenyl group),and is more preferably a phenyl group.

Preferably, at least one Tr has a substituent represented by thefollowing general formula (2). Among plural Tr's, one or more may havethe substituent represented by the general formula (2), but preferablytwo of them have the substituent. When two Tr's have a group representedby the general formula (2), the total of the groups represented by thegeneral formula (2) is preferably 1 to 5, more preferably 1 to 4, evenmore preferably 1 to 3.

Tr⁴-CO—  General Formula (2)

In the general formula (2), Tr⁴ represents a substituted orunsubstituted triphenylenyl group. The bonding position to the carbonylgroup (—CO—) in the triphenylenyl group is not specifically defined, butis preferably the 2-position. In the methine group not bonding to thecarbonyl group in the triphenylenyl group, the hydrogen atom may besubstituted with a substituent, or may not be substituted. For thedescription and the preferred range of the substituent that maysubstitute in the triphenylenyl group, the description and the preferredrange of the substituent that may substitute in the triphenylenyl groupof Tr may be referred to.

When plural Tr's exist inside the molecule of the compound representedby the general formula (1), the plural Tr's may be the same as ordifferent from each other, but are preferably the same. When pluralTr⁴'s represented by the general formula (2) exist inside the moleculeof the compound represented by the general formula (1), the plural Tr⁴'smay be the same as or different from each other, but are preferably thesame.

The compound represented by the general formula (1) preferably contains1 to 6 carbonyl groups, more preferably 1 to 3 carbonyl groups. Further,the compound represented by the general formula (1) preferably has apartial structure with a carbonyl group bonding to the 2-position, the3-position, the 6-position, the 7-position, the 10-position or the11-position of the triphenylene ring inside the molecule, and morepreferably, all the carbonyl groups bonding to the triphenylene ringexisting inside the molecule bond to the 2-position, the 3-position, the6-position, the 7-position, the 10-position or the 11-position of thetriphenylene ring.

Examples of the substituent of the aromatic hydrocarbon group that Z mayrepresent, the substituent that may substitute in the triphenylenylgroup of Tr and Tr⁴, and the substituent of the substituted alkyl groupand the substituted aryl group that may substitute in the aromatichydrocarbon group of the triphenylenyl group include a hydroxy group, ahalogen atom, a cyano group, an alkyl group having 1 to 20 carbon atoms,an alkoxy group having 1 to 20 carbon atoms, an alkylthio group having 1to 20 carbon atoms, an alkyl-substituted amino group having 1 to 20carbon atoms, an acyl group having 2 to 20 carbon atoms, an aryl grouphaving 6 to 40 carbon atoms, a heteroaryl group having 3 to 40 carbonatoms, an alkenyl group having 2 to 10 carbon atoms, an alkynyl grouphaving 2 to 10 carbon atoms, an alkoxycarbonyl group having 2 to 10carbon atoms, an alkylsulfonyl group having 1 to 10 carbon atoms, ahaloalkyl group having 1 to 10 carbon atoms, an amide group, analkylamide group having 2 to 10 carbon atoms, a trialkylsilyl grouphaving 3 to 20 carbon atoms, a trialkylsilylalkyl group having 4 to 20carbon atoms, a trialkylsilylalkenyl group having 5 to 20 carbon atoms,trialkylsilylalkynyl group having 5 to 20 carbon atoms, a nitro group, asubstituent represented by the above-mentioned general formula (2), etc.Among these examples, the substituents that may be further substitutedwith a substituent may be substituted. More preferred substituentsinclude a halogen atom, a cyano group, a substituted or unsubstitutedalkyl group having 1 to 20 carbon atoms, an alkoxy group having 1 to 20carbon atoms, a substituted or unsubstituted aryl group having 6 to 40carbon atoms, a substituted or unsubstituted heteroaryl group having 3to 40 carbon atoms, and a dialkyl-substituted amino group having 1 to 20carbon atoms. Even more preferred substituents include a fluorine atom,a chlorine atom, a cyano group, a substituted or unsubstituted alkylgroup having 1 to 10 carbon atoms, a substituted or unsubstituted alkoxygroup having 1 to 10 carbon atoms, a substituted or unsubstituted arylgroup having 6 to 15 carbon atoms, a substituted or unsubstitutedheteroaryl group having 3 to 12 carbon atoms, and a substituentrepresented by the general formula (2).

In the following, specific examples of the compound represented by thegeneral formula (1) are exemplified. However, the compound representedby the general formula (1) that is usable in the present inventionshould not be interpreted in a limited way by these examples. In thecompounds represented by the following formulae, R represents a methylgroup, a phenyl group, a benzoyl group, a triphenylenyl group or atriphenylenylcarbonyl group. Plural R's each representing thesubstituent may be the same as or different from each other.

The molecular weight of the compound represented by the general formula(1) is, for example, in the case of using it by forming an organic layerthat contains a compound represented by the general formula (1)according to a vapor deposition method, preferably 1500 or less, morepreferably 1200 or less, even more preferably 1000 or less, still morepreferably 800 or less. The lower limit of the molecular weight is themolecular weight of the smallest compound represented by the generalformula (1).

The compound represented by the general formula (1) may be formed into afilm according to a coating method irrespective of the molecular weightthereof. According to a coating method, even a compound having arelatively large molecular weight can be formed into a film.

By applying the present invention, it may be taken into consideration touse a compound containing plural structures represented by the generalformula (1) in the molecule thereof, as a host material for delayedfluorescent materials.

For example, a polymerizable group is previously introduced in thestructure represented by the general formula (1), and it may be takeninto consideration to use a polymer obtained through polymerization ofthe polymerizable group as a host material for delayed fluorescentmaterials. Specifically, a monomer containing a polymerizable functionalgroup in any of Tr and Z in the general formula (1) is prepared, andthis is homo-polymerized singly or copolymerized with any other monomerto give a polymer having a repeating unit, and use of the polymer as ahost material for delayed fluorescent materials may be taken intoconsideration. Alternatively, compounds each having a structurerepresented by the general formula (1) are coupled to give a dimer or atrimer, and use of these as a host material for delayed fluorescentmaterials may be taken into consideration.

Examples of the polymer having a repeating unit that contains astructure represented by the general formula (1) include polymerscontaining a structure represented by the following general formula (5)or (6).

In the general formulae (5) and (6), Q represents a group containing thestructure represented by the general formula (1), and L¹ and L² eachrepresent a linking group. The carbon number of the linking group ispreferably 0 to 20, more preferably 1 to 15, even more preferably 2 to10. The linking group preferably has a structure represented by—X¹¹-L¹¹-. Here, X¹¹ represents an oxygen atom or a sulfur atom, and ispreferably an oxygen atom. L¹¹ represents a linking group, and ispreferably a substituted or unsubstituted alkylene group or asubstituted or unsubstituted arylene group, more preferably asubstituted or unsubstituted alkylene group having 1 to 10 carbon atomsor a substituted or unsubstituted phenylene group.

In the general formulae (5) and (6), R¹⁰¹, R¹⁰², R¹⁰³ and R¹⁰⁴ eachindependently represent a substituent. Preferably, they each are asubstituted or unsubstituted alkyl group having 1 to 6 carbon atoms, asubstituted or unsubstituted alkoxy group having 1 to 6 carbon atoms, ora halogen atom, more preferably an unsubstituted alkyl group having 1 to3 carbon atoms, an unsubstituted alkoxy group having 1 to 3 carbonatoms, a fluorine atom or a chlorine atom, and even more preferably anunsubstituted alkyl group having 1 to 3 carbon atoms, or anunsubstituted alkoxy group having 1 to 3 carbon atoms.

The linking group represented by L¹ and L² may bond to any of Tr and Zin the structure of the general formula (1) that constitutes Q, or toTr⁴ in the general formula (2). Two or more linking groups may bond toone Q to form a crosslinked structure or a network structure.

Specific structural examples of the repeating unit include structuresrepresented by the following formulae (7) to (10).

Polymers having a repeating unit of the formulae (7) to (10) may besynthesized by previously introducing a hydroxy group into any of Tr andZ in a structure of the general formula (1), then introducing apolymerizable group into the structure through reaction with any of thefollowing compounds via the hydroxy group serving as a linker, andpolymerizing the polymerizable group.

The polymer having a structure represented by the general formula (1) inthe molecule may be a polymer containing a repeating unit alone having astructure represented by the general formula (1) or may be a polymercontaining a repeating unit having any other structure. The repeatingunit having a structure represented by the general formula (1) containedin the polymer may be one type alone or may contain two or more types ofrepeating units. A repeating unit not having a structure represented bythe general formula (1) includes those derived from monomers to be usedin ordinary copolymerization. For example, there are mentioned repeatingunits derived from monomers having an ethylenic unsaturated bond such asethylene, styrene, etc.

[Compound Represented by General Formula (3)]

Among the compounds represented by the general formula (1), compoundsrepresented by the following general formula (3) are novel compounds.

[Chem. 6]

Tr¹-CO-Tr²  General Formula (3)

In the general formula (3), Tr¹ and Tr² each independently represent asubstituted or unsubstituted triphenylenyl group, and Tr¹ and Tr² may bethe same as or different from each other.

For the description and the preferred range of Tr¹ and Tr² in thegeneral formula (3), the description of Tr in the general formula (1)may be referred to.

[Synthesis Method for Compound Represented by General Formula (3)]

The compound represented by the general formula (3) may be synthesizedby combining known reactions. For example, the compound of the generalformula (3) where Tr¹ and Tr² are unsubstituted triphenylenyl groups maybe synthesized according to the reaction shown by the following formula.

X in the above reaction formula represents a halogen atom, including afluorine atom, a chlorine atom, a bromine atom and an iodine atom, andis preferably a chlorine atom, a bromine atom or an iodine atom.

For the details of the reaction, Synthesis Examples to be givenhereinunder may be referred to.

In addition, the compound represented by the general formula (3) mayalso be synthesized by combining any other known synthesis reactions.

[Compound Represented by General Formula (4)]

Among the compounds represented by the general formula (1), compoundsrepresented by the following general formula (4) are also novelcompounds.

(Tr³)_(n1)-Z¹  General Formula (4)

In the general formula (4), Tr³ represents a substituted orunsubstituted triphenylenyl group, and plural Tr³'s existing in thegeneral formula (4) may be the same as or different from each other. Z¹represents a substituted or unsubstituted n-valent aromatic hydrocarbongroup. n1 represents an integer of 2 to 6. For the description and thepreferred range of Tr³, Z¹ and n1 in the general formula (4), thedescription of Tr, Z and n in the general formula (1) may be referredto. However, at least one of Tr³ and Z¹ is substituted with asubstituted or unsubstituted alkyl group or a substituted orunsubstituted aryl group. Among Tr³ and Z¹, one or more Tr³'s or one Z¹alone, or one or more Tr³'s and Z¹ may be substituted with a substitutedor unsubstituted alkyl group or a substituted or unsubstituted arylgroup. Here, when all Tr³'s are unsubstituted, Z¹ is a benzene ringresidue substituted with a phenyl group or a methyl group and bonds toTr³ at least at the 1-position and the 3-position, or is a biphenylresidue substituted with a phenyl group.

[Synthesis Method for Compound Represented by General Formula (4)]

The compound represented by the general formula (4) may be synthesizedby combining known reactions. For example, a compound represented by thegeneral formula (4) where Tr³ is an unsubstituted triphenylenyl group,Z¹ is a benzene residue with a methyl group substituting in the5-position, and Z¹ bonds to Tr³ at the 1-position and the 3-position maybe synthesized according to the reaction shown by the following formula.

X in the above reaction formula represents a halogen atom, including afluorine atom, a chlorine atom, a bromine atom and an iodine atom, andis preferably a chlorine atom, a bromine atom or an iodine atom.

For the details of the reaction, Synthesis Examples to be givenhereinunder may be referred to. In addition, the compound represented bythe general formula (4) may also be synthesized by combining any otherknown synthesis reactions.

Triphenylene derivatives (halide derivatives, borate derivatives) thatare the starting materials for synthesizing the compounds represented bythe general formulae (3) and (4) can be synthesized according to themethod described in PCT Int. Appl., 2013085243, PCT Int. Appl.,2013073896, PCT Int. Appl., 2012002221, or are available as commercialproducts.

[Organic Light-Emitting Device]

The compound represented by the general formula (1) of the invention isuseful as a host material for a delayed fluorescent material in anorganic light emitting device. Accordingly, the compound represented bythe general formula (1) of the invention may be effectively used as hostmaterial in an organic light-emitting device that uses a delayedfluorescent material as a light-emitting material therein. For example,it is presumed that, in an organic light-emitting device having alight-emitting layer that contains a host material of the compoundrepresented by the general formula (1) and a delayed fluorescentmaterial, the energy generated inside the molecule of the compoundrepresented by the general formula (1) can be efficiently transferred tothe delayed fluorescent material, and accordingly, the delayedfluorescent material can efficiently radiate delayed fluorescence.Consequently, the driving voltage for the organic light-emitting deviceof the type is low and the device can realize a high light emissionefficiency. Further, the organic light-emitting device is almost freefrom a problem of brightness reduction with the lapse of driving time,and can realize a long lifetime. This is presumed because the compoundrepresented by the general formula (1) could have high stability ascompared with a host material having a carbazole ring such as CBP.

Here, in order that the organic light-emitting device can express a highlight emission efficiency, it is important to use a delayed fluorescentmaterial as a light-emitting material, as combined with the compoundrepresented by the general formula (1) of the present invention. Theprinciple of realizing a high light emission efficiency by the use of adelayed fluorescent material may be described as follows for an organicelectroluminescence device as an example.

In an organic electroluminescence device, carriers are injected from ananode and a cathode to a light emitting material to form an excitedstate for the light emitting material, with which light is emitted. Inthe case of a carrier injection type organic electroluminescence device,in general, excitons that are excited to the excited singlet state are25% of the total excitons generated, and the remaining 75% thereof areexcited to the excited triplet state. Accordingly, the use ofphosphorescence, which is light emission from the excited triplet state,provides a high energy use efficiency. However, the excited tripletstate has a long lifetime and thus causes saturation of the excitedstate and deactivation of energy through mutual action with the excitonsin the excited triplet state, and therefore the quantum yield ofphosphorescence may generally be often not high. A delayed fluorescentmaterial emits fluorescent light through the mechanism that the energyof excitons transits to the excited triplet state through intersystemcrossing or the like, and then transits to the excited singlet statethrough reverse intersystem crossing due to triplet-triplet annihilationor absorption of thermal energy, thereby emitting fluorescent light. Itis considered that among the materials, a thermal activation typedelayed fluorescent material emitting light through absorption ofthermal energy is particularly useful for an organic electroluminescencedevice. In the case where a delayed fluorescent material is used in anorganic electroluminescence device, the excitons in the excited singletstate normally emit fluorescent light. On the other hand, the excitonsin the excited triplet state emit fluorescent light through intersystemcrossing to the excited singlet state by absorbing the heat generated bythe device. At this time, the light emitted through reverse intersystemcrossing from the excited triplet state to the excited singlet state hasthe same wavelength as fluorescent light since it is light emission fromthe excited singlet state, but has a longer lifetime (light emissionlifetime) than the normal fluorescent light and phosphorescent light,and thus the light is observed as fluorescent light that is delayed fromthe normal fluorescent light and phosphorescent light. The light may bedefined as delayed fluorescent light. The use of the thermal activationtype exciton transition mechanism may raise the proportion of thecompound in the excited singlet state, which is generally formed in aproportion only of 25%, to 25% or more through the absorption of thethermal energy after the carrier injection. A compound that emits strongfluorescent light and delayed fluorescent light at a low temperature oflower than 100° C. undergoes the intersystem crossing from the excitedtriplet state to the excited singlet state sufficiently with the heat ofthe device, thereby emitting delayed fluorescent light, and thus the useof the compound may drastically enhance the light emission efficiency.

By using the compound represented by the general formula (1) of theinvention as a host material for a delayed fluorescent material, therecan be provided excellent organic light-emitting devices such as organicphotoluminescence devices (organic PL devices), organicelectroluminescence devices (organic EL devices), etc. An organicphotoluminescence device has a structure that contains a substratehaving formed thereon at least a light-emitting layer. An organicelectroluminescence device has a structure containing at least an anode,a cathode and an organic layer formed between the anode and the cathode.The organic layer contains at least a light-emitting layer, and may beformed only of a light-emitting layer, or may have one or more organiclayer in addition to the light-emitting layer. Examples of the organiclayer include a hole transport layer, a hole injection layer, anelectron barrier layer, a hole barrier layer, an electron injectionlayer, an electron transport layer and an exciton barrier layer. Thehole transport layer may be a hole injection and transport layer havinga hole injection function, and the electron transport layer may be anelectron injection and transport layer having an electron injectionfunction. A specific structural example of an organicelectroluminescence device is shown in FIG. 1. In FIG. 1, the numeral 1denotes a substrate, 2 denotes an anode, 3 denotes a hole injectionlayer, 4 denotes a hole transport layer, 5 denotes a light-emittinglayer, 6 denotes an electron transport layer, and 7 denotes a cathode.

The members and the layers of the organic electroluminescence devicewill be described below. The descriptions for the substrate and thelight-emitting layer may also be applied to the substrate and thelight-emitting layer of the organic photoluminescence device.

(Substrate)

The organic electroluminescence device of the invention is preferablysupported by a substrate. The substrate is not particularly limited andmay be those that have been commonly used in an organicelectroluminescence device, and examples thereof used include thoseformed of glass, transparent plastics, quartz and silicon.

(Anode)

The anode of the organic electroluminescence device used is preferablyformed of as an electrode material include a metal, an alloy or anelectroconductive compound each having a large work function (4 eV ormore), or a mixture thereof. Specific examples of the electrode materialinclude a metal, such as Au, and an electroconductive transparentmaterial, such as CuI, indium tin oxide (ITO), SnO₂ and ZnO. A materialthat is amorphous and is capable of forming a transparentelectroconductive film, such as IDIXO (In₂O₃—ZnO), may also be used. Theanode may be formed in such a manner that the electrode material isformed into a thin film by such a method as vapor deposition orsputtering, and the film is patterned into a desired pattern by aphotolithography method, or in the case where the pattern may notrequire high accuracy (for example, approximately 100 μm or more), thepattern may be formed with a mask having a desired shape on vapordeposition or sputtering of the electrode material. In alternative, inthe case where a material capable of being applied as a coating, such asan organic electroconductive compound, is used, a wet film formingmethod, such as a printing method and a coating method, may be used. Inthe case where emitted light is to be taken out through the anode, theanode preferably has a transmittance of more than 10%, and the anodepreferably has a sheet resistance of several hundred ohm per square orless. The thickness thereof may be generally selected from a range offrom 10 to 1,000 nm, and preferably from 10 to 200 nm, while dependingon the material used.

(Cathode)

The cathode is preferably formed of as an electrode material including ametal having a small work function (4 eV or less) (referred to as anelectron injection metal), an alloy or an electroconductive compound, ora mixture thereof. Specific examples of the electrode material includesodium, a sodium-potassium alloy, magnesium, lithium, a magnesium-cuppermixture, a magnesium-silver mixture, a magnesium-aluminum mixture, amagnesium-indium mixture, an aluminum-aluminum oxide (Al₂O₃) mixture,indium, a lithium-aluminum mixture, and a rare earth metal. Among these,a mixture of an electron injection metal and a second metal that is astable metal having a larger work function than the electron injectionmetal, for example, a magnesium-silver mixture, a magnesium-aluminummixture, a magnesium-indium mixture, an aluminum-aluminum oxide (Al₂O₃)mixture, a lithium-aluminum mixture, and aluminum, are preferred fromthe standpoint of the electron injection property and the durabilityagainst oxidation and the like. The cathode may be produced by formingthe electrode material into a thin film by such a method as vapordeposition or sputtering. The cathode preferably has a sheet resistanceof several hundred ohm per square or less, and the thickness thereof maybe generally selected from a range of from 10 nm to 5 μm, and preferablyfrom 50 to 200 nm. For transmitting the emitted light, any one of theanode and the cathode of the organic electroluminescence device ispreferably transparent or translucent, thereby enhancing the lightemission luminance.

The cathode may be formed with the electroconductive transparentmaterials described for the anode, thereby forming a transparent ortranslucent cathode, and by applying the cathode, a device having ananode and a cathode, both of which have transmittance, may be produced.

(Light-Emitting Layer)

The light-emitting layer is a layer, in which holes and electronsinjected from the anode and the cathode, respectively, are recombined toform excitons, and the layer contains a delayed fluorescent material anda host material for the delayed fluorescent material. As the hostmaterial for the delayed fluorescent material, one kind or two or morekinds selected from the group of compounds represented by the generalformula (1) of the invention can be used. In order that the organicelectroluminescence device and the organic photoluminescence device ofthe invention exhibit a high light emission efficiency, it is importantthat the singlet excitons and the triplet excitons generated in thedelayed fluorescent material are confined in the delayed fluorescentmaterial. Accordingly, as the host material for the delayed fluorescentmaterial, those of the compounds represented by the general formula (1)are preferably so selected that at least any one of the excited singletenergy and the excited triplet energy thereof could be higher than thatof the delayed fluorescent material. Consequently, the singlet excitonsand the triplet excitons generated in the delayed fluorescent materialcan be confined in the molecule of the delayed fluorescent material,thereby eliciting the light emission efficiency of the materialsufficiently.

In addition, the light-emitting layer may contain any other hostmaterial along with the host material for the delayed fluorescentmaterial of the present invention. As the other host material, acompound having carrier transportability and excited energytransferability is preferably used. Accordingly, electrons and holes canbe readily injected into the light-emitting layer and the probability ofrecombining the holes and the electrons increases. In addition, theexcited energy formed by recombination of holes and electrons can bereadily transferred to the delayed fluorescent material and the delayedfluorescent material can be thereby efficiently excited. As a result,the device can realize a high brightness at a low driving voltage. Thehost material having carrier transportability and excited energytransferability may be suitably selected from known host materials, andfor the same reason as that for the compound represented by the generalformula (1), it is desirable to select those of such that at least anyone of the excited singlet energy and the excited triplet energy thereofis higher than that of the delayed fluorescent material. Specifically,as the other host material, a compound having a carbazole ring such asCBP or the like can be used.

In the organic light-emitting device or the organic electroluminescencedevice of the present invention, light emission forms from the delayedfluorescent material contained in the light-emitting layer. The lightemission includes both fluorescence emission and delayed fluorescenceemission. However, the light emission may partly include light emissionfrom the compound represented by the general formula (1) as a partthereof.

The content of the delayed fluorescent material in the light-emittinglayer is preferably 0.1 to 50% by mass, more preferably 0.1 to 20% bymass, even more preferably 0.5 to 5% by mass.

In the case where the host material for delayed fluorescent materials ofthe present invention is combined with any other host material for useherein, the ratio by mass of the two may be any arbitrary ratio, but ispreferably 90/10 to 10/90, more preferably 75/25 to 25/75, even morepreferably 66/33 to 33/66.

(Injection Layer)

The injection layer is a layer that is provided between the electrodeand the organic layer, for decreasing the driving voltage and enhancingthe light emission luminance, and includes a hole injection layer and anelectron injection layer, which may be provided between the anode andthe light-emitting layer or the hole transport layer and between thecathode and the light-emitting layer or the electron transport layer.The injection layer may be provided depending on necessity.

(Barrier Layer)

The barrier layer is a layer that is capable of inhibiting charges(electrons or holes) and/or excitons present in the light-emitting layerfrom being diffused outside the light-emitting layer. The electronbarrier layer may be disposed between the light-emitting layer and thehole transport layer, and inhibits electrons from passing through thelight-emitting layer toward the hole transport layer. Similarly, thehole barrier layer may be disposed between the light-emitting layer andthe electron transport layer, and inhibits holes from passing throughthe light-emitting layer toward the electron transport layer. Thebarrier layer may also be used for inhibiting excitons from beingdiffused outside the light-emitting layer. Thus, the electron barrierlayer and the hole barrier layer each may also have a function as anexciton barrier layer. The term “the electron barrier layer” or “theexciton barrier layer” referred herein is intended to include a layerthat has both the functions of an electron barrier layer and an excitonbarrier layer by one layer.

(Hole Barrier Layer)

The hole barrier layer has the function of an electron transport layerin a broad sense. The hole barrier layer has a function of inhibitingholes from reaching the electron transport layer while transportingelectrons, and thereby enhances the recombination probability ofelectrons and holes in the light-emitting layer. As the material for thehole barrier layer, the materials for the electron transport layerdescribed later may be used depending on necessity.

(Electron Barrier Layer)

The electron barrier layer has the function of transporting holes in abroad sense. The electron barrier layer has a function of inhibitingelectrons from reaching the hole transport layer while transportingholes, and thereby enhances the recombination probability of electronsand holes in the light-emitting layer.

(Exciton Barrier Layer)

The exciton barrier layer is a layer for inhibiting excitons generatedthrough recombination of holes and electrons in the light-emitting layerfrom being diffused to the charge transport layer, and the use of thelayer inserted enables effective confinement of excitons in thelight-emitting layer, and thereby enhances the light emission efficiencyof the device. The exciton barrier layer may be inserted adjacent to thelight-emitting layer on any of the side of the anode and the side of thecathode, and on both the sides. Specifically, in the case where theexciton barrier layer is present on the side of the anode, the layer maybe inserted between the hole transport layer and the light-emittinglayer and adjacent to the light-emitting layer, and in the case wherethe layer is inserted on the side of the cathode, the layer may beinserted between the light-emitting layer and the cathode and adjacentto the light-emitting layer. Between the anode and the exciton barrierlayer that is adjacent to the light-emitting layer on the side of theanode, a hole injection layer, an electron barrier layer and the likemay be provided, and between the cathode and the exciton barrier layerthat is adjacent to the light-emitting layer on the side of the cathode,an electron injection layer, an electron transport layer, a hole barrierlayer and the like may be provided. In the case where the barrier layeris provided, the material used for the barrier layer preferably hasexcited singlet energy and excited triplet energy, at least one of whichis higher than the excited singlet energy and the excited triplet energyof the delayed fluorescent material, respectively.

(Hole Transport Layer)

The hole transport layer is formed of a hole transporting materialhaving a function of transporting holes, and the hole transport layermay be provided as a single layer or plural layers.

The hole transporting material has one of injection or transportingproperty of holes and barrier property of electrons, and may be any ofan organic material and an inorganic material. Examples of known holetransporting materials that may be used herein include a triazolederivative, an oxadiazole derivative, an imidazole derivative, acarbazole derivative, an indolocarbazole derivative, a polyarylalkanederivative, a pyrazoline derivative, a pyrazolone derivative, aphenylenediamine derivative, an arylamine derivative, anamino-substituted chalcone derivative, an oxazole derivative, astyrylanthracene derivative, a fluorenone derivative, a hydrazonederivative, a stilbene derivative, a silazane derivative, an anilinecopolymer and an electroconductive polymer oligomer, particularly athiophene oligomer. Among these, a porphyrin compound, an aromatictertiary amine compound and a styrylamine compound are preferably used,and an aromatic tertiary amine compound is more preferably used.

Electron Transport Layer

The electron transport layer is formed of a material having a functionof transporting electrons, and the electron transport layer may beprovided as a single layer or plural layers.

The electron transporting material (which may also function as a holebarrier material in some cases) needs only to have a function oftransporting electrons, which are injected from the cathode, to thelight-emitting layer. Examples of the electron transport layer that maybe used herein include a nitro-substituted fluorene derivative, adiphenylquinone derivative, a thiopyran dioxide derivative,carbodiimide, a fluorenylidene methane derivative, anthraquinodimethaneand anthrone derivatives, and an oxadiazole derivative. The electrontransporting material used may be a thiadiazole derivative obtained byreplacing the oxygen atom of the oxadiazole ring of the oxadiazolederivative by a sulfur atom, or a quinoxaline derivative having aquinoxaline ring, which is known as an electron attracting group.Furthermore, polymer materials having these materials introduced to thepolymer chain or having these materials used as the main chain of thepolymer may also be used.

In the production of the organic electroluminescence device, thecompound represented by the general formula (1) may be used not only inthe light-emitting layer but also in the other layers than thelight-emitting layer. In this case, the compound represented by thegeneral formula (1) used in the light-emitting layer and the compoundrepresented by the general formula (1) used in the other layers than thelight-emitting layer may be the same as or different from each other.For example, the compound represented by the general formula (1) may beused in the injection layer, the barrier layer, the hole barrier layer,the electron barrier layer, the exciton barrier layer, the holetransport layer, the electron transport layer and the like describedabove. The film forming method of the layers are not particularlylimited, and the layers may be produced by any of a dry process and awet process.

Specific examples of preferred materials that may be used in the organicelectroluminescence device are shown below, but the materials that maybe used in the invention are not construed as being limited to theexample compounds. The compound that is shown as a material having aparticular function may also be used as a material having anotherfunction. In the structural formulae of the example compounds shownbelow, R, R′ and R₁ to R₁₀ each independently represent a hydrogen atomor a substituent. X represents a carbon atom or a hetero atom to form aring skeleton, n represents an integer of 3 to 5, Y represents asubstituent, and m represents an integer of 0 or more.

The delayed fluorescent material to be combined with the host materialfor delayed fluorescent materials that contains the compound representedby the general formula (1) is a compound capable of radiating delayedfluorescence. Preferred examples of the delayed fluorescent material areshown below, however, the delayed fluorescent material to be employed inthe present invention is not limited to those shown below.

As a preferred delayed fluorescent material, a compound represented bythe following general formula can be mentioned. The entire descriptionof WO 2013/154064 including the paragraphs 0008 to 0048 and 0095 to 0133is incorporated herein by reference as a part of the description of thepresent application.

[In the general formula (101), at least one of R¹ to R⁵ represents acyano group, at least one of R¹ to R⁵ represents a group represented bythe following general formula (111), and the balance of R¹ to R⁵ eachrepresent a hydrogen atom or a substituent.]

[In the general formula (111), R²¹ to R²⁸ each independently represent ahydrogen atom or a substituent, provided that at least one of thefollowing conditions <A> and <B> is satisfied:

<A> R²⁵ and R²⁶ together form a single bond, and

<B> R²⁷ and R²⁸ each represent an atomic group necessary for forming asubstituted or unsubstituted benzene ring as combined together.]

Here, at least one of R¹ to R⁵ preferably represents a group representedby any one of the following general formulae (112) to (115).

[In the general formula (112), R³¹ to R³⁸ each independently represent ahydrogen atom or a substituent.]

[In the general formula (113), R⁴¹ to R⁴⁶ each independently represent ahydrogen atom or a substituent.]

[In the general formula (114), R⁵¹ to R⁶² each independently represent ahydrogen atom or a substituent.]

[In the general formula (115), R⁷¹ to R⁸⁰ each independently represent ahydrogen atom or a substituent.]

Specific examples of the compounds include the compounds shown in thefollowing tables. In the case where two or more groups represented byany one of the general formulae (112) to (115) are present in themolecule of the following example compounds, all the groups have thesame structure. The formulae (121) to (124) in the tables represent thefollowing formulae, respectively, and n represents the number of therepeating units.

TABLE 1 Compound General formula (101) General formula (112) No. R¹ R²R³ R⁴ R⁵ R³¹, R³⁸ R³², R³⁷ R³³, R³⁶ R³⁴, R³⁵ 1′ General General CNGeneral General H H H H formula (112) formula (112) formula (112)formula (112) 2′ General General CN General General H CH₃ H H formula(112) formula (112) formula (112) formula (112) 3′ General General CNGeneral General H CH₃O H H formula (112) formula (112) formula (112)formula (112) 4′ General General CN General General H H CH₃ H formula(112) formula (112) formula (112) formula (112) 5′ General General CNGeneral General H H CH₃O H formula (112) formula (112) formula (112)formula (112) 6′ General General CN General General H H t-C₄H₉ H formula(112) formula (112) formula (112) formula (112) 7′ General General CNGeneral General H H Cl H formula (112) formula (112) formula (112)formula (112) 8′ General General CN General General H H F H formula(112) formula (112) formula (112) formula (112) 9′ General General CNGeneral General H H H CH₃ formula (112) formula (112) formula (112)formula (112) 10′ General General CN General General H H H CH₃O formula(112) formula (112) formula (112) formula (112) 11′ General General CNGeneral H H H H H formula (112) formula (112) formula (112) 12′ GeneralGeneral CN General H H CH₃ H H formula (112) formula (112) formula (112)13′ General General CN General H H CH₃O H H formula (112) formula (112)formula (112) 14′ General General CN General H H H CH₃ H formula (112)formula (112) formula (112) 15′ General General CN General H H H CH₃O Hformula (112) formula (112) formula (112) 16′ General General CN GeneralH H H t-C₄H₉ H formula (112) formula (112) formula (112) 17′ GeneralGeneral CN General H H H Cl H formula (112) formula (112) formula (112)18′ General General CN General H H H F H formula (112) formula (112)formula (112) 19′ General General CN General H H H H CH₃ formula (112)formula (112) formula (112) 20′ General General CN General H H H H CH₃Oformula (112) formula (112) formula (112) 21′ General General CN H H H HH H formula (112) formula (112) 22′ General General CN H H H CH₃ H Hformula (112) formula (112) 23′ General General CN H H H CH₃O H Hformula (112) formula (112) 24′ General General CN H H H H CH₃ H formula(112) formula (112) 25′ General General CN H H H H CH₃O H formula (112)formula (112) 26′ General General CN H H H H t-C₄H₉ H formula (112)formula (112) 27′ General General CN H H H H Cl H formula (112) formula(112) 28′ General General CN H H H H F H formula (112) formula (112) 29′General General CN H H H H H CH₃ formula (112) formula (112) 30′ GeneralGeneral CN H H H H H CH₃O formula (112) formula (112) 31′ General H CNGeneral H H H H H formula (112) formula (112) 32′ General H CN General HH CH₃ H H formula (112) formula (112) 33′ General H CN General H H CH₃OH H formula (112) formula (112) 34′ General H CN General H H H CH₃ Hformula (112) formula (112) 35′ General H CN General H H H CH₃O Hformula (112) formula (112) 36′ General H CN General H H H t-C₄H₉ Hformula (112) formula (112) 37′ General H CN General H H H Cl H formula(112) formula (112) 38′ General H CN General H H H F H formula (112)formula (112) 39′ General H CN General H H H H CH₃ formula (112) formula(112) 40′ General H CN General H H H H CH₃O formula (112) formula (112)41′ General H CN H General H H H H formula (112) formula (112) 42′General H CN H General H CH₃ H H formula (112) formula (112) 43′ GeneralH CN H General H CH₃O H H formula (112) formula (112) 44′ General H CN HGeneral H H CH₃ H formula (112) formula (112) 45′ General H CN H GeneralH H CH₃O H formula (112) formula (112) 46′ General H CN H General H Ht-C₄H₉ H formula (112) formula (112) 47′ General H CN H General H H Cl Hformula (112) formula (112) 48′ General H CN H General H H F H formula(112) formula (112) 49′ General H CN H General H H H CH₃ formula (112)formula (112) 50′ General H CN H General H H H CH₃O formula (112)formula (112) 51′ General H CN H H H H H H formula (112) 52′ General HCN H H H CH₃ H H formula (112) 53′ General H CN H H H CH₃O H H formula(112) 54′ General H CN H H H H CH₃ H formula (112) 55′ General H CN H HH H CH₃O H formula (112) 56′ General H CN H H H H t-C₄H₉ H formula (112)57′ General H CN H H H H Cl H formula (112) 58′ General H CN H H H H F Hformula (112) 59′ General H CN H H H H H CH₃ formula (112) 60′ General HCN H H H H H CH₃O formula (112) 61′ General General CN General F H H H Hformula (112) formula (112) formula (112) 62′ General General CN GeneralF H CH₃ H H formula (112) formula (112) formula (112) 63′ GeneralGeneral CN General F H CH₃O H H formula (112) formula (112) formula(112) 64′ General General CN General F H H CH₃ H formula (112) formula(112) formula (112) 65′ General General CN General F H H CH₃O H formula(112) formula (112) formula (112) 66′ General General CN General F H Ht-C₄H₉ H formula (112) formula (112) formula (112) 67′ General GeneralCN General F H H Cl H formula (112) formula (112) formula (112) 68′General General CN General F H H F H formula (112) formula (112) formula(112) 69′ General General CN General F H H H CH₃ formula (112) formula(112) formula (112) 70′ General General CN General F H H H CH₃O formula(112) formula (112) formula (112) 71′ General General CN F F H H H Hformula (112) formula (112) 72′ General General CN F F H CH₃ H H formula(112) formula (112) 73′ General General CN F F H CH₃O H H formula (112)formula (112) 74′ General General CN F F H H CH₃ H formula (112) formula(112) 75′ General General CN F F H H CH₃O H formula (112) formula (112)76′ General General CN F F H H t-C₄H₉ H formula (112) formula (112) 77′General General CN F F H H Cl H formula (112) formula (112) 78′ GeneralGeneral CN F F H H F H formula (112) formula (112) 79′ General GeneralCN F F H H H CH₃ formula (112) formula (112) 80′ General General CN F FH H H CH₃O formula (112) formula (112) 81′ General F CN General F H H HH formula (112) formula (112) 82′ General F CN General F H CH₃ H Hformula (112) formula (112) 83′ General F CN General F H CH₃O H Hformula (112) formula (112) 84′ General F CN General F H H CH₃ H formula(112) formula (112) 85′ General F CN General F H H CH₃O H formula (112)formula (112) 86′ General F CN General F H H t-C₄H₉ H formula (112)formula (112) 87′ General F CN General F H H Cl H formula (112) formula(112) 88′ General F CN General F H H F H formula (112) formula (112) 89′General F CN General F H H H CH₃ formula (112) formula (112) 90′ GeneralF CN General F H H H CH₃O formula (112) formula (112) 91′ General F CN FGeneral H H H H formula (112) formula (112) 92′ General F CN F General HCH₃ H H formula (112) formula (112) 93′ General F CN F General H CH₃O HH formula (112) formula (112) 94′ General F CN F General H H CH₃ Hformula (112) formula (112) 95′ General F CN F General H H CH₃O Hformula (112) formula (112) 96′ General F CN F General H H t-C₄H₉ Hformula (112) formula (112) 97′ General F CN F General H H Cl H formula(112) formula (112) 98′ General F CN F General H H F H formula (112)formula (112) 99′ General F CN F General H H H CH₃ formula (112) formula(112) 100′ General F CN F General H H H CH₃O formula (112) formula (112)101′ General F CN F F H H H H formula (112) 102′ General F CN F F H CH₃H H formula (112) 103′ General F CN F F H CH₃O H H formula (112) 104′General F CN F F H H CH₃ H formula (112) 105′ General F CN F F H H CH₃OH formula (112) 106′ General F CN F F H H t-C₄H₉ H formula (112) 107′General F CN F F H H Cl H formula (112) 108′ General F CN F F H H F Hformula (112) 109′ General F CN F F H H H CH₃ formula (112) 110′ GeneralF CN F F H H H CH₃O formula (112) 111′ General General CN General OH H HH H formula (112) formula (112) formula (112) 112′ General General CNGeneral OH H CH₃ H H formula (112) formula (112) formula (112) 113′General General CN General OH H CH₃O H H formula (112) formula (112)formula (112) 114′ General General CN General OH H H CH₃ H formula (112)formula (112) formula (112) 115′ General General CN General OH H H CH₃OH formula (112) formula (112) formula (112) 116′ General General CNGeneral OH H H t-C₄H₉ H formula (112) formula (112) formula (112) 117′General General CN General OH H H Cl H formula (112) formula (112)formula (112) 118′ General General CN General OH H H F H formula (112)formula (112) formula (112) 119′ General General CN General OH H H H CH₃formula (112) formula (112) formula (112) 120′ General General CNGeneral OH H H H CH₃O formula (112) formula (112) formula (112) 121′General General CN OH OH H H H H formula (112) formula (112) 122′General General CN OH OH H CH₃ H H formula (112) formula (112) 123′General General CN OH OH H CH₃O H H formula (112) formula (112) 124′General General CN OH OH H H CH₃ H formula (112) formula (112) 125′General General CN OH OH H H CH₃O H formula (112) formula (112) 126′General General CN OH OH H H t-C₄H₉ H formula (112) formula (112) 127′General General CN OH OH H H Cl H formula (112) formula (112) 128′General General CN OH OH H H F H formula (112) formula (112) 129′General General CN OH OH H H H CH₃ formula (112) formula (112) 130′General General CN OH OH H H H CH₃O formula (112) formula (112) 131′General OH CN General OH H H H H formula (112) formula (112) 132′General OH CN General OH H CH₃ H H formula (112) formula (112) 133′General OH CN General OH H CH₃O H H formula (112) formula (112) 134′General OH CN General OH H H CH₃ H formula (112) formula (112) 135′General OH CN General OH H H CH₃O H formula (112) formula (112) 136′General OH CN General OH H H t-C₄H₉ H formula (112) formula (112) 137′General OH CN General OH H H Cl H formula (112) formula (112) 138′General OH CN General OH H H F H formula (112) formula (112) 139′General OH CN General OH H H H CH₃ formula (112) formula (112) 140′General OH CN General OH H H H CH₃O formula (112) formula (112) 141′General OH CN OH General H H H H formula (112) formula (112) 142′General OH CN OH General H CH₃ H H formula (112) formula (112) 143′General OH CN OH General H CH₃O H H formula (112) formula (112) 144′General OH CN OH General H H CH₃ H formula (112) formula (112) 145′General OH CN OH General H H CH₃O H formula (112) formula (112) 146′General OH CN OH General H H t-C₄H₉ H formula (112) formula (112) 147′General OH CN OH General H H Cl H formula (112) formula (112) 148′General OH CN OH General H H F H formula (112) formula (112) 149′General OH CN OH General H H H CH₃ formula (112) formula (112) 150′General OH CN OH General H H H CH₃O formula (112) formula (112) 151′General OH CN OH OH H H H H formula (112) 152′ General OH CN OH OH H CH₃H H formula (112) 153′ General OH CN OH OH H CH₃O H H formula (112) 154′General OH CN OH OH H H CH₃ H formula (112) 155′ General OH CN OH OH H HCH₃O H formula (112) 156′ General OH CN OH OH H H t-C₄H₉ H formula (112)157′ General OH CN OH OH H H Cl H formula (112) 158′ General OH CN OH OHH H F H formula (112) 159′ General OH CN OH OH H H H CH₃ formula (112)160′ General OH CN OH OH H H H CH₃O formula (112) 161′ General GeneralCN General Cl H H H H formula (112) formula (112) formula (112) 162′General General CN General Cl H CH₃ H H formula (112) formula (112)formula (112) 163′ General General CN General Cl H CH₃O H H formula(112) formula (112) formula (112) 164′ General General CN General Cl H HCH₃ H formula (112) formula (112) formula (112) 165′ General General CNGeneral Cl H H CH₃O H formula (112) formula (112) formula (112) 166′General General CN General Cl H H t-C₄H₉ H formula (112) formula (112)formula (112) 167′ General General CN General Cl H H Cl H formula (112)formula (112) formula (112) 168′ General General CN General Cl H H F Hformula (112) formula (112) formula (112) 169′ General General CNGeneral Cl H H H CH₃ formula (112) formula (112) formula (112) 170′General General CN General Cl H H H CH₃O formula (112) formula (112)formula (112) 171′ General General CN General F H H H H formula (112)formula (112) formula (112) 172′ General General CN General F H CH₃ H Hformula (112) formula (112) formula (112) 173′ General General CNGeneral F H CH₃O H H formula (112) formula (112) formula (112) 174′General General CN General F H H CH₃ H formula (112) formula (112)formula (112) 175′ General General CN General F H H CH₃O H formula (112)formula (112) formula (112) 176′ General General CN General F H H t-C₄H₉H formula (112) formula (112) formula (112) 177′ General General CNGeneral F H H Cl H formula (112) formula (112) formula (112) 178′General General CN General F H H F H formula (112) formula (112) formula(112) 179′ General General CN General F H H H CH₃ formula (112) formula(112) formula (112) 180′ General General CN General F H H H CH₃O formula(112) formula (112) formula (112) 181′ General General CN General CH₃O HH H H formula (112) formula (112) formula (112) 182′ General General CNGeneral CH₃O H CH₃ H H formula (112) formula (112) formula (112) 183′General General CN General CH₃O H CH₃O H H formula (112) formula (112)formula (112) 184′ General General CN General CH₃O H H CH₃ H formula(112) formula (112) formula (112) 185′ General General CN General CH₃O HH CH₃O H formula (112) formula (112) formula (112) 186′ General GeneralCN General CH₃O H H t-C₄H₉ H formula (112) formula (112) formula (112)187′ General General CN General CH₃O H H Cl H formula (112) formula(112) formula (112) 188′ General General CN General CH₃O H H F H formula(112) formula (112) formula (112) 189′ General General CN General C₂H₅OH H H CH₃ formula (112) formula (112) formula (112) 190′ General GeneralCN General C₂H₅O H H H CH₃O formula (112) formula (112) formula (112)191′ General General CN General C₂H₅O H H H H formula (112) formula(112) formula (112) 192′ General General CN General C₂H₅O H CH₃ H Hformula (112) formula (112) formula (112) 193′ General General CNGeneral C₂H₅O H CH₃O H H formula (112) formula (112) formula (112) 194′General General CN General C₂H₅O H H CH₃ H formula (112) formula (112)formula (112) 195′ General General CN General C₂H₅O H H CH₃O H formula(112) formula (112) formula (112) 196′ General General CN General C₂H₅OH H t-C₄H₉ H formula (112) formula (112) formula (112) 197′ GeneralGeneral CN General C₂H₅O H H Cl H formula (112) formula (112) formula(112) 198′ General General CN General C₂H₅O H H F H formula (112)formula (112) formula (112) 199′ General General CN General C₂H₅O H H HCH₃ formula (112) formula (112) formula (112) 200′ General General CNGeneral C₂H₅O H H H CH₃O formula (112) formula (112) formula (112) 201′General General CN General C₆H₅O H H H H formula (112) formula (112)formula (112) 202′ General General CN General C₆H₅O H CH₃ H H formula(112) formula (112) formula (112) 203′ General General CN General C₆H₅OH CH₃O H H formula (112) formula (112) formula (112) 204′ GeneralGeneral CN General C₆H₅O H H CH₃ H formula (112) formula (112) formula(112) 205′ General General CN General C₆H₅O H H CH₃O H formula (112)formula (112) formula (112) 206′ General General CN General C₆H₅O H Ht-C₄H₉ H formula (112) formula (112) formula (112) 207′ General GeneralCN General C₆H₅O H H Cl H formula (112) formula (112) formula (112) 208′General General CN General C₆H₅O H H F H formula (112) formula (112)formula (112) 209′ General General CN General C₆H₅O H H H CH₃ formula(112) formula (112) formula (112) 210′ General General CN General C₆H₅OH H H CH₃O formula (112) formula (112) formula (112) 211′ GeneralGeneral CN General Formula H H H H formula (112) formula (112) formula(112) (121) 212′ General General CN General Formula H CH₃ H H formula(112) formula (112) formula (112) (121) 213′ General General CN GeneralFormula H CH₃O H H formula (112) formula (112) formula (112) (121) 214′General General CN General Formula H H CH₃ H formula (112) formula (112)formula (112) (121) 215′ General General CN General Formula H H CH₃O Hformula (112) formula (112) formula (112) (121) 216′ General General CNGeneral Formula H H t-C₄H₉ H formula (112) formula (112) formula (112)(121) 217′ General General CN General Formula H H Cl H formula (112)formula (112) formula (112) (121) 218′ General General CN GeneralFormula H H F H formula (112) formula (112) formula (112) (121) 219′General General CN General Formula H H H CH₃ formula (112) formula (112)formula (112) (121) 220′ General General CN General Formula H H H CH₃Oformula (112) formula (112) formula (112) (121) 221′ General General CNGeneral Formula H H H H formula (112) formula (112) formula (112) (122)222′ General General CN General Formula H CH₃ H H formula (112) formula(112) formula (112) (122) 223′ General General CN General Formula H CH₃OH H formula (112) formula (112) formula (112) (122) 224′ General GeneralCN General Formula H H CH₃ H formula (112) formula (112) formula (112)(122) 225′ General General CN General Formula H H CH₃O H formula (112)formula (112) formula (112) (122) 226′ General General CN GeneralFormula H H t-C₄H₉ H formula (112) formula (112) formula (112) (122)227′ General General CN General Formula H H Cl H formula (112) formula(112) formula (112) (122) 228′ General General CN General Formula H H FH formula (112) formula (112) formula (112) (122) 229′ General GeneralCN General Formula H H H CH₃ formula (112) formula (112) formula (112)(122) 230′ General General CN General Formula H H H CH₃O formula (112)formula (112) formula (112) (122) 231′ General General CN GeneralFormula H H H H formula (112) formula (112) formula (112) (123) 232′General General CN General Formula H CH₃ H H formula (112) formula (112)formula (112) (123) 233′ General General CN General Formula H CH₃O H Hformula (112) formula (112) formula (112) (123) 234′ General General CNGeneral Formula H H CH₃ H formula (112) formula (112) formula (112)(123) 235′ General General CN General Formula H H CH₃O H formula (112)formula (112) formula (112) (123) 236′ General General CN GeneralFormula H H t-C₄H₉ H formula (112) formula (112) formula (112) (123)237′ General General CN General Formula H H Cl H formula (112) formula(112) formula (112) (123) 238′ General General CN General Formula H H FH formula (112) formula (112) formula (112) (123) 239′ General GeneralCN General Formula H H H CH₃ formula (112) formula (112) formula (112)(123) 240′ General General CN General Formula H H H CH₃O formula (112)formula (112) formula (112) (123) 241′ General General CN GeneralFormula H H H H formula (112) formula (112) formula (112) (124) 242′General General CN General Formula H CH₃ H H formula (112) formula (112)formula (112) (124) 243′ General General CN General Formula H CH₃O H Hformula (112) formula (112) formula (112) (124) 244′ General General CNGeneral Formula H H CH₃ H formula (112) formula (112) formula (112)(124) 245′ General General CN General Formula H H CH₃O H formula (112)formula (112) formula (112) (124) 246′ General General CN GeneralFormula H H t-C₄H₉ H formula (112) formula (112) formula (112) (124)247′ General General CN General Formula H H Cl H formula (112) formula(112) formula (112) (124) 248′ General General CN General Formula H H FH formula (112) formula (112) formula (112) (124) 249′ General GeneralCN General Formula H H H CH₃ formula (112) formula (112) formula (112)(124) 250′ General General CN General Formula H H H CH₃O formula (112)formula (112) formula (112) (124) 251′ General General CN GeneralGeneral H C₆H₅ H H formula (112) formula (112) formula (112) formula(112) 252′ General General CN General General H H C₆H₅ H formula (112)formula (112) formula (112) formula (112) 253′ General General CNGeneral H H C₆H₅ H H formula (112) formula (112) formula (112) 254′General General CN General H H H C₆H₅ H formula (112) formula (112)formula (112) 255′ General General CN H H H C₆H₅ H H formula (112)formula (112) 256′ General General CN H H H H C₆H₅ H formula (112)formula (112) 257′ General H CN General H H C₆H₅ H H formula (112)formula (112) 258′ General H CN General H H H C₆H₅ H formula (112)formula (112) 259′ General H CN H General H C₆H₅ H H formula (112)formula (112) 260′ General H CN H General H H C₆H₅ H formula (112)formula (112) 261′ General H CN H H H C₆H₅ H H formula (112) 262′General H CN H H H H C₆H₅ H formula (112) 263′ General General CNGeneral F H C₆H₅ H H formula (112) formula (112) formula (112) 264′General General CN General F H H C₆H₅ H formula (112) formula (112)formula (112) 265′ General General CN F F H C₆H₅ H H formula (112)formula (112) 266′ General General CN F F H H C₆H₅ H formula (112)formula (112) 267′ General F CN General F H C₆H₅ H H formula (112)formula (112) 268′ General F CN General F H H C₆H₅ H formula (112)formula (112) 269′ General F CN F General H C₆H₅ H H formula (112)formula (112) 270′ General F CN F General H H C₆H₅ H formula (112)formula (112) 271′ General F CN F F H C₆H₅ H H formula (112) 272′General F CN F F H H C₆H₅ H formula (112) 273′ General General CNGeneral OH H C₆H₅ H H formula (112) formula (112) formula (112) 274′General General CN General OH H H C₆H₅ H formula (112) formula (112)formula (112) 275′ General General CN OH OH H C₆H₅ H H formula (112)formula (112) 276′ General General CN OH OH H H C₆H₅ H formula (112)formula (112) 277′ General OH CN General OH H C₆H₅ H H formula (112)formula (112) 278′ General OH CN General OH H H C₆H₅ H formula (112)formula (112) 279′ General OH CN OH General H C₆H₅ H H formula (112)formula (112) 280′ General OH CN OH General H H C₆H₅ H formula (112)formula (112) 281′ General OH CN OH OH H C₆H₅ H H formula (112) 282′General OH CN OH OH H H C₆H₅ H formula (112) 283′ General General CNGeneral Cl H C₆H₅ H H formula (112) formula (112) formula (112) 284′General General CN General Cl H H C₆H₅ H formula (112) formula (112)formula (112) 285′ General General CN General F H C₆H₅ H H formula (112)formula (112) formula (112) 286′ General General CN General F H H C₆H₅ Hformula (112) formula (112) formula (112) 287′ General General CNGeneral CH₃O H C₆H₅ H H formula (112) formula (112) formula (112) 288′General General CN General CH₃O H H C₆H₅ H formula (112) formula (112)formula (112) 289′ General General CN General C₂H₅O H C₆H₅ H H formula(112) formula (112) formula (112) 290′ General General CN General C₂H₅OH H C₆H₅ H formula (112) formula (112) formula (112) 291′ GeneralGeneral CN General C₆H₅O H C₆H₅ H H formula (112) formula (112) formula(112) 292′ General General CN General C₆H₅O H H C₆H₅ H formula (112)formula (112) formula (112) 293′ General General CN General Formula HC₆H₅ H H formula (112) formula (112) formula (112) (121) 294′ GeneralGeneral CN General Formula H H C₆H₅ H formula (112) formula (112)formula (112) (121) 295′ General General CN General Formula H C₆H₅ H Hformula (112) formula (112) formula (112) (122) 296′ General General CNGeneral Formula H H C₆H₅ H formula (112) formula (112) formula (112)(122) 297′ General General CN General Formula H C₆H₅ H H formula (112)formula (112) formula (112) (123) 298′ General General CN GeneralFormula H H C₆H₅ H formula (112) formula (112) formula (112) (123) 299′General General CN General Formula H C₆H₅ H H formula (112) formula(112) formula (112) (124) 300′ General General CN General Formula H HC₆H₅ H formula (112) formula (112) formula (112) (124)

TABLE 2 Compound General formula (101) General formula (112) No. R¹ R²R³ R⁴ R⁵ R³¹, R³⁸ R³², R³⁷ R³³, R³⁶ R³⁴, R³⁵ 301 General CN GeneralGeneral General H H H H formula (112) formula (112) formula (112)formula (112) 302 General CN General General General H CH₃ H H formula(112) formula (112) formula (112) formula (112) 303 General CN GeneralGeneral General H CH₃O H H formula (112) formula (112) formula (112)formula (112) 304 General CN General General General H H CH₃ H formula(112) formula (112) formula (112) formula (112) 305 General CN GeneralGeneral General H H CH₃O H formula (112) formula (112) formula (112)formula (112) 306 General CN General General General H H t-C₄H₉ Hformula (112) formula (112) formula (112) formula (112) 307 General CNGeneral General General H H Cl H formula (112) formula (112) formula(112) formula (112) 308 General CN General General General H H F Hformula (112) formula (112) formula (112) formula (112) 309 General CNGeneral General General H H H CH₃ formula (112) formula (112) formula(112) formula (112) 310 General CN General General General H H H CH₃Oformula (112) formula (112) formula (112) formula (112) 311 General CNGeneral General H H H H H formula (112) formula (112) formula (112) 312General CN General General H H H CH₃ H formula (112) formula (112)formula (112) 313 General CN General General H H H CH₃O H formula (112)formula (112) formula (112) 314 General CN General H General H H H Hformula (112) formula (112) formula (112) 315 General CN General HGeneral H H CH₃ H formula (112) formula (112) formula (112) 316 GeneralCN General H General H H CH₃O H formula (112) formula (112) formula(112) 317 General CN H General General H H H H formula (112) formula(112) formula (112) 318 General CN H General General H H CH₃ H formula(112) formula (112) formula (112) 319 General CN H General General H HCH₃O H formula (112) formula (112) formula (112) 320 H CN GeneralGeneral General H H H H formula (112) formula (112) formula (112) 321 HCN General General General H H CH₃ H formula (112) formula (112) formula(112) 322 H CN General General General H H CH₃O H formula (112) formula(112) formula (112) 323 General CN General H H H H H H formula (112)formula (112) 324 General CN General H H H H CH₃ H formula (112) formula(112) 325 General CN General H H H H CH₃O H formula (112) formula (112)326 General CN H General H H H H H formula (112) formula (112) 327General CN H General H H H CH₃ H formula (112) formula (112) 328 GeneralCN H General H H H CH₃O H formula (112) formula (112) 329 H CN GeneralGeneral H H H H H formula (112) formula (112) 330 H CN General General HH H CH₃ H formula (112) formula (112) 331 H CN General General H H HCH₃O H formula (112) formula (112) 332 General CN H H General H H H Hformula (112) formula (112) 333 General CN H H General H H CH₃ H formula(112) formula (112) 334 General CN H H General H H CH₃O H formula (112)formula (112) 335 H CN General H General H H H H formula (112) formula(112) 336 H CN General H General H H CH₃ H formula (112) formula (112)337 H CN General H General H H CH₃O H formula (112) formula (112) 338 HCN H General General H H H H formula (112) formula (112) 339 H CN HGeneral General H H CH₃ H formula (112) formula (112) 340 H CN H GeneralGeneral H H CH₃O H formula (112) formula (112) 341 General CN H H H H HH H formula (112) 342 General CN H H H H H CH₃ H formula (112) 343General CN H H H H H CH₃O H formula (112) 344 H CN General H H H H H Hformula (112) 345 H CN General H H H H CH₃ H formula (112) 346 H CNGeneral H H H H CH₃O H formula (112) 347 H CN H General H H H H Hformula (112) 348 H CN H General H H H CH₃ H formula (112) 349 H CN HGeneral H H H CH₃O H formula (112) 350 General CN General General F H HH H formula (112) formula (112) formula (112) 351 General CN GeneralGeneral F H H CH₃ H formula (112) formula (112) formula (112) 352General CN General General F H H CH₃O H formula (112) formula (112)formula (112) 353 General CN General F General H H H H formula (112)formula (112) formula (112) 354 General CN General F General H H CH₃ Hformula (112) formula (112) formula (112) 355 General CN General FGeneral H H CH₃O H formula (112) formula (112) formula (112) 356 GeneralCN F General General H H H H formula (112) formula (112) formula (112)357 General CN F General General H H CH₃ H formula (112) formula (112)formula (112) 358 General CN F General General H H CH₃O H formula (112)formula (112) formula (112) 359 F CN General General General H H H Hformula (112) formula (112) formula (112) 360 F CN General GeneralGeneral H H CH₃ H formula (112) formula (112) formula (112) 361 F CNGeneral General General H H CH₃O H formula (112) formula (112) formula(112) 362 General CN General F F H H H H formula (112) formula (112) 363General CN General F F H H CH₃ H formula (112) formula (112) 364 GeneralCN General F F H H CH₃O H formula (112) formula (112) 365 General CN FGeneral F H H H H formula (112) formula (112) 366 General CN F General FH H CH₃ H formula (112) formula (112) 367 General CN F General F H HCH₃O H formula (112) formula (112) 368 F CN General General F H H H Hformula (112) formula (112) 369 F CN General General F H H CH₃ H formula(112) formula (112) 370 F CN General General F H H CH₃O H formula (112)formula (112) 371 General CN F F General H H H H formula (112) formula(112) 372 General CN F F General H H CH₃ H formula (112) formula (112)373 General CN F F General H H CH₃O H formula (112) formula (112) 374 FCN General F General H H H H formula (112) formula (112) 375 F CNGeneral F General H H CH₃ H formula (112) formula (112) 376 F CN GeneralF General H H CH₃O H formula (112) formula (112) 377 F CN F GeneralGeneral H H H H formula (112) formula (112) 378 F CN F General General HH CH₃ H formula (112) formula (112) 379 F CN F General General H H CH₃OH formula (112) formula (112) 380 General CN F F F H H H H formula (112)381 General CN F F F H H CH₃ H formula (112) 382 General CN F F F H HCH₃O H formula (112) 383 F CN General F F H H H H formula (112) 384 F CNGeneral F F H H CH₃ H formula (112) 385 F CN General F F H H CH₃O Hformula (112) 386 F CN F General F H H H H formula (112) 387 F CN FGeneral F H H CH₃ H formula (112) 388 F CN F General F H H CH₃O Hformula (112) 389 General CN General General OH H H H H formula (112)formula (112) formula (112) 390 General CN General General OH H H CH₃ Hformula (112) formula (112) formula (112) 391 General CN General GeneralOH H H CH₃O H formula (112) formula (112) formula (112) 392 General CNGeneral OH General H H H H formula (112) formula (112) formula (112) 393General CN General OH General H H CH H formula (112) formula (112)formula (112) 394 General CN General OH General H H CH₃O H formula (112)formula (112) formula (112) 395 General CN General OH General H H t-C₄H₉H formula (112) formula (112) formula (112) 396 General CN General OHGeneral H H Cl H formula (112) formula (112) formula (112) 397 GeneralCN General OH General H H F H formula (112) formula (112) formula (112)398 General CN OH General General H H H H formula (112) formula (112)formula (112) 399 General CN OH General General H H CH₃ H formula (112)formula (112) formula (112) 400 General CN OH General General H H CH₃O Hformula (112) formula (112) formula (112) 401 OH CN General GeneralGeneral H H H H formula (112) formula (112) formula (112) 402 OH CNGeneral General General H H CH₃ H formula (112) formula (112) formula(112) 403 OH CN General General General H H CH₃O H formula (112) formula(112) formula (112) 404 General CN General OH OH H H H H formula (112)formula (112) 405 General CN General OH OH H H CH₃ H formula (112)formula (112) 406 General CN General OH OH H H CH₃O H formula (112)formula (112) 407 General CN OH General OH H H H H formula (112) formula(112) 408 General CN OH General OH H H CH₃ H formula (112) formula (112)409 General CN OH General OH H H CH₃O H formula (112) formula (112) 410OH CN General General OH H H H H formula (112) formula (112) 411 OH CNGeneral General OH H H CH₃ H formula (112) formula (112) 412 OH CNGeneral General OH H H CH₃O H formula (112) formula (112) 413 General CNOH OH General H H H H formula (112) formula (112) 414 General CN OH OHGeneral H H CH₃ H formula (112) formula (112) 415 General CN OH OHGeneral H H CH₃O H formula (112) formula (112) 416 OH CN General OHGeneral H H H H formula (112) formula (112) 417 OH CN General OH GeneralH H CH₃ H formula (112) formula (112) 418 OH CN General OH General H HCH₃O H formula (112) formula (112) 419 OH CN OH General General H H H Hformula (112) formula (112) 420 OH CN OH General General H H CH₃ Hformula (112) formula (112) 421 OH CN OH General General H H CH₃O Hformula (112) formula (112) 422 General CN OH OH OH H H H H formula(112) 423 General CN OH OH OH H H CH₃ H formula (112) 424 General CN OHOH OH H H CH₃O H formula (112) 425 OH CN General OH OH H H H H formula(112) 426 OH CN General OH OH H H CH₃ H formula (112) 427 OH CN GeneralOH OH H H CH₃O H formula (112) 428 OH CN OH General OH H H H H formula(112) 429 OH CN OH General OH H H CH₃ H formula (112) 430 OH CN OHGeneral OH H H CH₃O H formula (112) 431 OH CN OH OH General H H H Hformula (112) 432 OH CN OH OH General H H CH₃ H formula (112) 433 OH CNOH OH General H H CH₃O H formula (112) 434 General CN General Cl GeneralH H H H formula (112) formula (112) formula (112) 435 General CN GeneralCl General H H CH₃ H formula (112) formula (112) formula (112) 436General CN General Cl General H H CH₃O H formula (112) formula (112)formula (112) 437 General CN General Cl General H H t-C₄H₉ H formula(112) formula (112) formula (112) 438 General CN General Cl General H HCl H formula (112) formula (112) formula (112) 439 General CN General ClGeneral H H F H formula (112) formula (112) formula (112) 440 General CNGeneral F General H H H H formula (112) formula (112) formula (112) 441General CN General F General H H CH₃ H formula (112) formula (112)formula (112) 442 General CN General F General H H CH₃O H formula (112)formula (112) formula (112) 443 General CN General F General H H t-C₄H₉H formula (112) formula (112) formula (112) 444 General CN General FGeneral H H Cl H formula (112) formula (112) formula (112) 445 GeneralCN General F General H H F H formula (112) formula (112) formula (112)446 General CN General CH₃O General H H H H formula (112) formula (112)formula (112) 447 General CN General CH₃O General H H CH₃ H formula(112) formula (112) formula (112) 448 General CN General CH₃O General HH CH₃O H formula (112) formula (112) formula (112) 449 General CNGeneral CH₃O General H H t-C₄H₉ H formula (112) formula (112) formula(112) 450 General CN General CH₃O General H H Cl H formula (112) formula(112) formula (112) 451 General CN General CH₃O General H H F H formula(112) formula (112) formula (112) 452 General CN General C₂H₅O General HH H H formula (112) formula (112) formula (112) 453 General CN GeneralC₂H₅O General H H CH₃ H formula (112) formula (112) formula (112) 454General CN General C₂H₅O General H H CH₃O H formula (112) formula (112)formula (112) 455 General CN General C₂H₅O General H H t-C₄H₉ H formula(112) formula (112) formula (112) 456 General CN General C₂H₅O General HH Cl H formula (112) formula (112) formula (112) 457 General CN GeneralC₂H₅O General H H F H formula (112) formula (112) formula (112) 458General CN General C₆H₅O General H H H H formula (112) formula (112)formula (112) 459 General CN General C₆H₅O General H H CH₃ H formula(112) formula (112) formula (112) 460 General CN General C₆H₅O General HH CH₃O H formula (112) formula (112) formula (112) 461 General CNGeneral C₆H₅O General H H t-C₄H₉ H formula (112) formula (112) formula(112) 462 General CN General C₆H₅O General H H Cl H formula (112)formula (112) formula (112) 463 General CN General C₆H₅O General H H F Hformula (112) formula (112) formula (112) 464 General CN General FormulaGeneral H H H H formula (112) formula (112) (121) formula (112) 465General CN General Formula General H H CH₃ H formula (112) formula (112)(121) formula (112) 466 General CN General Formula General H H CH₃O Hformula (112) formula (112) (121) formula (112) 467 General CN GeneralFormula General H H t-C₄H₉ H formula (112) formula (112) (121) formula(112) 468 General CN General Formula General H H Cl H formula (112)formula (112) (121) formula (112) 469 General CN General Formula GeneralH H F H formula (112) formula (112) (121) formula (112) 470 General CNGeneral Formula General H H H H formula (112) formula (112) (122)formula (112) 471 General CN General Formula General H H CH₃ H formula(112) formula (112) (122) formula (112) 472 General CN General FormulaGeneral H H CH₃O H formula (112) formula (112) (122) formula (112) 473General CN General Formula General H H t-C₄H₉ H formula (112) formula(112) (122) formula (112) 474 General CN General Formula General H H ClH formula (112) formula (112) (122) formula (112) 475 General CN GeneralFormula General H H F H formula (112) formula (112) (122) formula (112)476 General CN General Formula General H H H H formula (112) formula(112) (123) formula (112) 477 General CN General Formula General H H CH₃H formula (112) formula (112) (123) formula (112) 478 General CN GeneralFormula General H H CH₃O H formula (112) formula (112) (123) formula(112) 479 General CN General Formula General H H t-C₄H₉ H formula (112)formula (112) (123) formula (112) 480 General CN General Formula GeneralH H Cl H formula (112) formula (112) (123) formula (112) 481 General CNGeneral Formula General H H F H formula (112) formula (112) (123)formula (112) 482 General CN General Formula General H H H H formula(112) formula (112) (124) formula (112) 483 General CN General FormulaGeneral H H CH₃ H formula (112) formula (112) (124) formula (112) 484General CN General Formula General H H CH₃O H formula (112) formula(112) (124) formula (112) 485 General CN General Formula General H Ht-C₄H₉ H formula (112) formula (112) (124) formula (112) 486 General CNGeneral Formula General H H Cl H formula (112) formula (112) (124)formula (112) 487 General CN General Formula General H H F H formula(112) formula (112) (124) formula (112) 488 General CN General GeneralGeneral H C₆H₅ H H formula (112) formula (112) formula (112) formula(112) 489 General CN General General General H H C₆H₅ H formula (112)formula (112) formula (112) formula (112) 490 General CN General GeneralH H C₆H₅ H H formula (112) formula (112) formula (112) 491 General CNGeneral General H H H C₆H₅ H formula (112) formula (112) formula (112)492 General CN General H General H C₆H₅ H H formula (112) formula (112)formula (112) 493 General CN General H General H H C₆H₅ H formula (112)formula (112) formula (112) 494 General CN H General General H C₆H₅ H Hformula (112) formula (112) formula (112) 495 General CN H GeneralGeneral H H C₆H₅ H formula (112) formula (112) formula (112) 496 H CNGeneral General General H C₆H₅ H H formula (112) formula (112) formula(112) 497 H CN General General General H H C₆H₅ H formula (112) formula(112) formula (112) 498 General CN General H H H C₆H₅ H H formula (112)formula (112) 499 General CN General H H H H C₆H₅ H formula (112)formula (112) 500-1 General CN H General H H C₆H₅ H H formula (112)formula (112) 500-2 General CN H General H H H C₆H₅ H formula (112)formula (112) 500-3 H CN General General H H C₆H₅ H H formula (112)formula (112) 500-4 H CN General General H H H C₆H₅ H formula (112)formula (112) 500-5 General CN H H General H C₆H₅ H H formula (112)formula (112) 500-6 General CN H H General H H C₆H₅ H formula (112)formula (112) 500-7 H CN General H General H C₆H₅ H H formula (112)formula (112) 500-8 H CN General H General H H C₆H₅ H formula (112)formula (112) 500-9 H CN H General General H C₆H₅ H H formula (112)formula (112) 500-10 H CN H General General H H C₆H₅ H formula (112)formula (112) 500-11 General CN H H H H C₆H₅ H H formula (112) 500-12General CN H H H H H C₆H₅ H formula (112) 500-13 H CN General H H H C₆H₅H H formula (112) 500-14 H CN General H H H H C₆H₅ H formula (112)500-15 H CN H General H H C₆H₅ H H formula (112) 500-16 H CN H General HH H C₆H₅ H formula (112) 500-17 General CN General General F H H C₆H₅ Hformula (112) formula (112) formula (112) 500-18 General CN General FGeneral H H C₆H₅ H formula (112) formula (112) formula (112) 500-19General CN F General General H H C₆H₅ H formula (112) formula (112)formula (112) 500-20 F CN General General General H H C₆H₅ H formula(112) formula (112) formula (112) 500-21 General CN General F F H H C₆H₅H formula (112) formula (112) 500-22 General CN F General F H H C₆H₅ Hformula (112) formula (112) 500-23 F CN General General F H H C₆H₅ Hformula (112) formula (112) 500-24 General CN F F General H H C₆H₅ Hformula (112) formula (112) 500-25 F CN General F General H H C₆H₅ Hformula (112) formula (112) 500-26 F CN F General General H H C₆H₅ Hformula (112) formula (112) 500-27 General CN F F F H H C₆H₅ H formula(112) 500-28 F CN General F F H H C₆H₅ H formula (112) 500-29 F CN FGeneral F H H C₆H₅ H formula (112) 500-30 General CN General General OHH H C₆H₅ H formula (112) formula (112) formula (112) 500-31 General CNGeneral OH General H H C₆H₅ H formula (112) formula (112) formula (112)500-32 General CN OH General General H H C₆H₅ H formula (112) formula(112) formula (112) 500-33 OH CN General General General H H C₆H₅ Hformula (112) formula (112) formula (112) 500-34 General CN General OHOH H H C₆H₅ H formula (112) formula (112) 500-35 General CN OH GeneralOH H H C₆H₅ H formula (112) formula (112) 500-36 OH CN General GeneralOH H H C₆H₅ H formula (112) formula (112) 500-37 General CN OH OHGeneral H H C₆H₅ H formula (112) formula (112) 500-38 OH CN General OHGeneral H H C₆H₅ H formula (112) formula (112) 500-39 OH CN OH GeneralGeneral H H C₆H₅ H formula (112) formula (112) 500-40 General CN OH OHOH H H C₆H₅ H formula (112) 500-41 OH CN General OH OH H H C₆H₅ Hformula (112) 500-42 OH CN OH General OH H H C₆H₅ H formula (112) 500-43OH CN OH OH General H H C₆H₅ H formula (112) 500-44 General CN GeneralCl General H H C₆H₅ H formula (112) formula (112) formula (112) 500-45General CN General F General H H C₆H₅ H formula (112) formula (112)formula (112) 500-46 General CN General CH₃O General H H C₆H₅ H formula(112) formula (112) formula (112) 500-47 General CN General C₂H₅OGeneral H H C₆H₅ H formula (112) formula (112) formula (112) 500-48General CN General C₆H₅O General H H C₆H₅ H formula (112) formula (112)formula (112) 500-49 General CN General Formula General H H C₆H₅ Hformula (112) formula (112) (121) formula (112) 500-50 General CNGeneral Formula General H H C₆H₅ H formula (112) formula (112) (122)formula (112) 500-51 General CN General Formula General H H C₆H₅ Hformula (112) formula (112) (123) formula (112) 500-52 General CNGeneral Formula General H H C₆H₅ H formula (112) formula (112) (124)formula (112)

TABLE 3 Compound General formula (101) General formula (112) No. R¹ R²R³ R⁴ R⁵ R³¹, R³⁸ R³², R³⁷ R³³, R³⁶ R³⁴, R³⁵ 501 CN General GeneralGeneral General H H H H formula (112) formula (112) formula (112)formula (112) 502 CN General General General General H CH₃ H H formula(112) formula (112) formula (112) formula (112) 503 CN General GeneralGeneral General H CH₃O H H formula (112) formula (112) formula (112)formula (112) 504 CN General General General General H H CH₃ H formula(112) formula (112) formula (112) formula (112) 505 CN General GeneralGeneral General H H CH₃O H formula (112) formula (112) formula (112)formula (112) 506 CN General General General General H H t-C₄H₉ Hformula (112) formula (112) formula (112) formula (112) 507 CN GeneralGeneral General General H H Cl H formula (112) formula (112) formula(112) formula (112) 508 CN General General General General H H F Hformula (112) formula (112) formula (112) formula (112) 509 CN GeneralGeneral General General H H H CH₃ formula (112) formula (112) formula(112) formula (112) 510 CN General General General General H H H CH₃Oformula (112) formula (112) formula (112) formula (112) 511 CN GeneralGeneral General H H H H H formula (112) formula (112) formula (112) 512CN General General General H H H CH₃ H formula (112) formula (112)formula (112) 513 CN General General General H H H CH₃O H formula (112)formula (112) formula (112) 514 CN General General H General H H H Hformula (112) formula (112) formula (112) 515 CN General General HGeneral H H CH₃ H formula (112) formula (112) formula (112) 516 CNGeneral General H General H H CH₃O H formula (112) formula (112) formula(112) 517 CN General General H H H H H H formula (112) formula (112) 518CN General General H H H H CH₃ H formula (112) formula (112) 519 CNGeneral General H H H H CH₃O H formula (112) formula (112) 520 CNGeneral H General H H H H H formula (112) formula (112) 521 CN General HGeneral H H H CH₃ H formula (112) formula (112) 522 CN General H GeneralH H H CH₃O H formula (112) formula (112) 523 CN H General General H H HH H formula (112) formula (112) 524 CN H General General H H H CH₃ Hformula (112) formula (112) 525 CN H General General H H H CH₃O Hformula (112) formula (112) 526 CN General H H General H H H H formula(112) formula (112) 527 CN General H H General H H CH₃ H formula (112)formula (112) 528 CN General H H General H H CH₃O H formula (112)formula (112) 529 CN General H H H H H H H formula (112) 530 CN GeneralH H H H H CH₃ H formula (112) 531 CN General H H H H H CH₃O H formula(112) 532 CN H General H H H H H H formula (112) 533 CN H General H H HH CH₃ H formula (112) 534 CN H General H H H H CH₃O H formula (112) 535CN General General General F H H H H formula (112) formula (112) formula(112) 536 CN General General General F H H CH₃ H formula (112) formula(112) formula (112) 537 CN General General General F H H CH₃O H formula(112) formula (112) formula (112) 538 CN General General F General H H HH formula (112) formula (112) formula (112) 539 CN General General FGeneral H H CH₃ H formula (112) formula (112) formula (112) 540 CNGeneral General F General H H CH₃O H formula (112) formula (112) formula(112) 541 CN General General F F H H H H formula (112) formula (112) 542CN General General F F H H CH₃ H formula (112) formula (112) 543 CNGeneral General F F H H CH₃O H formula (112) formula (112) 544 CNGeneral F General F H H H H formula (112) formula (112) 545 CN General FGeneral F H H CH₃ H formula (112) formula (112) 546 CN General F GeneralF H H CH₃O H formula (112) formula (112) 547 CN F General General F H HH H formula (112) formula (112) 548 CN F General General F H H CH₃ Hformula (112) formula (112) 549 CN F General General F H H CH₃O Hformula (112) formula (112) 550 CN General F F General H H H H formula(112) formula (112) 551 CN General F F General H H CH₃ H formula (112)formula (112) 552 CN General F F General H H CH₃O H formula (112)formula (112) 553 CN General F F F H H H H formula (112) 554 CN GeneralF F F H H CH₃ H formula (112) 555 CN General F F F H H CH₃O H formula(112) 556 CN F General F F H H H H formula (112) 557 CN F General F F HH CH₃ H formula (112) 558 CN F General F F H H CH₃O H formula (112) 559CN General General General OH H H H H formula (112) formula (112)formula (112) 560 CN General General General OH H H CH₃ H formula (112)formula (112) formula (112) 561 CN General General General OH H H CH₃O Hformula (112) formula (112) formula (112) 562 CN General General OHGeneral H H H H formula (112) formula (112) formula (112) 563 CN GeneralGeneral OH General H H CH₃ H formula (112) formula (112) formula (112)654 CN General General OH General H H CH₃O H formula (112) formula (112)formula (112) 565 CN General General OH General H H Cl H formula (112)formula (112) formula (112) 566 CN General General OH General H H F Hformula (112) formula (112) formula (112) 567 CN General General OH OH HH H H formula (112) formula (112) 568 CN General General OH OH H H CH₃ Hformula (112) formula (112) 569 CN General General OH OH H H CH₃O Hformula (112) formula (112) 570 CN General OH General OH H H H H formula(112) formula (112) 571 CN General OH General OH H H CH₃ H formula (112)formula (112) 572 CN General OH General OH H H CH₃O H formula (112)formula (112) 573 CN OH General General OH H H H H formula (112) formula(112) 574 CN OH General General OH H H CH₃ H formula (112) formula (112)575 CN OH General General OH H H CH₃O H formula (112) formula (112) 576CN General OH OH General H H H H formula (112) formula (112) 577 CNGeneral OH OH General H H CH₃ H formula (112) formula (112) 578 CNGeneral OH OH General H H CH₃O H formula (112) formula (112) 579 CNGeneral OH OH OH H H H H formula (112) 580 CN General OH OH OH H H CH₃ Hformula (112) 581 CN General OH OH OH H H CH₃O H formula (112) 582 CN OHGeneral OH OH H H H H formula (112) 583 CN OH General OH OH H H CH₃ Hformula (112) 584 CN OH General OH OH H H CH₃O H formula (112) 585 CNGeneral General Cl General H H H H formula (112) formula (112) formula(112) 586 CN General General Cl General H H CH₃ H formula (112) formula(112) formula (112) 587 CN General General Cl General H H CH₃O H formula(112) formula (112) formula (112) 588 CN General General Cl General H Ht-C₄H₉ H formula (112) formula (112) formula (112) 589 CN GeneralGeneral Cl General H H Cl H formula (112) formula (112) formula (112)590 CN General General Cl General H H F H formula (112) formula (112)formula (112) 591 CN General General F General H H H H formula (112)formula (112) formula (112) 592 CN General General F General H H CH₃ Hformula (112) formula (112) formula (112) 593 CN General General FGeneral H H CH₃O H formula (112) formula (112) formula (112) 594 CNGeneral General F General H H t-C₄H₉ H formula (112) formula (112)formula (112) 595 CN General General F General H H Cl H formula (112)formula (112) formula (112) 596 CN General General F General H H F Hformula (112) formula (112) formula (112) 597 CN General General CH₃OGeneral H H H H formula (112) formula (112) formula (112) 598 CN GeneralGeneral CH₃O General H H CH₃ H formula (112) formula (112) formula (112)599 CN General General CH₃O General H H CH₃O H formula (112) formula(112) formula (112) 600 CN General General CH₃O General H H t-C₄H₉ Hformula (112) formula (112) formula (112) 601 CN General General CH₃OGeneral H H Cl H formula (112) formula (112) formula (112) 602 CNGeneral General CH₃O General H H F H formula (112) formula (112) formula(112) 603 CN General General C₂H₅O General H H H H formula (112) formula(112) formula (112) 604 CN General General C₂H₅O General H H CH₃ Hformula (112) formula (112) formula (112) 605 CN General General C₂H₅OGeneral H H CH₃O H formula (112) formula (112) formula (112) 606 CNGeneral General C₂H₅O General H H t-C₄H₉ H formula (112) formula (112)formula (112) 607 CN General General C₂H₅O General H H Cl H formula(112) formula (112) formula (112) 608 CN General General C₂H₅O General HH F H formula (112) formula (112) formula (112) 609 CN General GeneralC₆H₅O General H H H H formula (112) formula (112) formula (112) 610 CNGeneral General C₆H₅O General H H CH₃ H formula (112) formula (112)formula (112) 611 CN General General C₆H₅O General H H CH₃O H formula(112) formula (112) formula (112) 612 CN General General C₆H₅O General HH t-C₄H₉ H formula (112) formula (112) formula (112) 613 CN GeneralGeneral C₆H₅O General H H Cl H formula (112) formula (112) formula (112)614 CN General General C₆H₅O General H H F H formula (112) formula (112)formula (112) 615 CN General General Formula General H H H H formula(112) formula (112) (121) formula (112) 616 CN General General FormulaGeneral H H CH₃ H formula (112) formula (112) (121) formula (112) 617 CNGeneral General Formula General H H CH₃O H formula (112) formula (112)(121) formula (112) 618 CN General General Formula General H H t-C₄H₉ Hformula (112) formula (112) (121) formula (112) 619 CN General GeneralFormula General H H Cl H formula (112) formula (112) (121) formula (112)620 CN General General Formula General H H F H formula (112) formula(112) (121) formula (112) 621 CN General General Formula General H H H Hformula (112) formula (112) (122) formula (112) 622 CN General GeneralFormula General H H CH₃ H formula (112) formula (112) (122) formula(112) 623 CN General General Formula General H H CH₃O H formula (112)formula (112) (122) formula (112) 624 CN General General Formula GeneralH H t-C₄H₉ H formula (112) formula (112) (122) formula (112) 625 CNGeneral General Formula General H H Cl H formula (112) formula (112)(122) formula (112) 626 CN General General Formula General H H F Hformula (112) formula (112) (122) formula (112) 627 CN General GeneralFormula General H H H H formula (112) formula (112) (123) formula (112)628 CN General General Formula General H H CH₃ H formula (112) formula(112) (123) formula (112) 629 CN General General Formula General H HCH₃O H formula (112) formula (112) (123) formula (112) 630 CN GeneralGeneral Formula General H H t-C₄H₉ H formula (112) formula (112) (123)formula (112) 631 CN General General Formula General H H Cl H formula(112) formula (112) (123) formula (112) 632 CN General General FormulaGeneral H H F H formula (112) formula (112) (123) formula (112) 633 CNGeneral General Formula General H H H H formula (112) formula (112)(124) formula (112) 634 CN General General Formula General H H CH₃ Hformula (112) formula (112) (124) formula (112) 635 CN General GeneralFormula General H H CH₃O H formula (112) formula (112) (124) formula(112) 636 CN General General Formula General H H t-C₄H₉ H formula (112)formula (112) (124) formula (112) 637 CN General General Formula GeneralH H Cl H formula (112) formula (112) (124) formula (112) 638 CN GeneralGeneral Formula General H H F H formula (112) formula (112) (124)formula (112) 639 CN General General General General H C₆H₅ H H formula(112) formula (112) formula (112) formula (112) 640 CN General GeneralGeneral General H H C₆H₅ H formula (112) formula (112) formula (112)formula (112) 641 CN General General General H H C₆H₅ H H formula (112)formula (112) formula (112) 642 CN General General General H H H C₆H₅ Hformula (112) formula (112) formula (112) 643 CN General General HGeneral H C₆H₅ H H formula (112) formula (112) formula (112) 644 CNGeneral General H General H H C₆H₅ H formula (112) formula (112) formula(112) 645 CN General General H H H C₆H₅ H H formula (112) formula (112)646 CN General General H H H H C₆H₅ H formula (112) formula (112) 647 CNGeneral H General H H C₆H₅ H H formula (112) formula (112) 648 CNGeneral H General H H H C₆H₅ H formula (112) formula (112) 649 CN HGeneral General H H C₆H₅ H H formula (112) formula (112) 650 CN HGeneral General H H H C₆H₅ H formula (112) formula (112) 651 CN H HGeneral General H C₆H₅ H H formula (112) formula (112) 652 CN H HGeneral General H H C₆H₅ H formula (112) formula (112) 653 CN General HH H H C₆H₅ H H formula (112) 654 CN General H H H H H C₆H₅ H formula(112) 655 CN H General H H H C₆H₅ H H formula (112) 656 CN H General H HH H C₆H₅ H formula (112) 657 CN General General General F H H C₆H₅ Hformula (112) formula (112) formula (112) 658 CN General General FGeneral H H C₆H₅ H formula (112) formula (112) formula (112) 659 CNGeneral General F F H H C₆H₅ H formula (112) formula (112) 660 CNGeneral F General F H H C₆H₅ H formula (112) formula (112) 661 CN FGeneral General F H H C₆H₅ H formula (112) formula (112) 662 CN F FGeneral General H H C₆H₅ H formula (112) formula (112) 663 CN General FF F H H C₆H₅ H formula (112) 664 CN F General F F H H C₆H₅ H formula(112) 665 CN General General General OH H H C₆H₅ H formula (112) formula(112) formula (112) 666 CN General General OH General H H C₆H₅ H formula(112) formula (112) formula (112) 667 CN General General OH OH H H C₆H₅H formula (112) formula (112) 668 CN General OH General OH H H C₆H₅ Hformula (112) formula (112) 669 CN OH General General OH H H C₆H₅ Hformula (112) formula (112) 670 CN OH OH General General H H C₆H₅ Hformula (112) formula (112) 671 CN General OH OH OH H H C₆H₅ H formula(112) 672 CN OH General OH OH H H C₆H₅ H formula (112) 673 CN GeneralGeneral Cl General H H C₆H₅ H formula (112) formula (112) formula (112)674 CN General General F General H H C₆H₅ H formula (112) formula (112)formula (112) 675 CN General General CH₃O General H H C₆H₅ H formula(112) formula (112) formula (112) 676 CN General General C₂H₅O General HH C₆H₅ H formula (112) formula (112) formula (112) 677 CN GeneralGeneral C₆H₅O General H H C₆H₅ H formula (112) formula (112) formula(112) 678 CN General General Formula General H H C₆H₅ H formula (112)formula (112) (121) formula (112) 679 CN General General Formula GeneralH H C₆H₅ H formula (112) formula (112) (122) formula (112) 680 CNGeneral General Formula General H H C₆H₅ H formula (112) formula (112)(123) formula (112) 681 CN General General Formula General H H C₆H₅ Hformula (112) formula (112) (124) formula (112)

TABLE 4 Compound General formula (101) No. R¹ R² R³ R⁴ R⁵ 701 Generalformula (113) General formula (113) CN General formula (113) Generalformula (113) 702 General formula (113) General formula (113) CN Generalformula (113) General formula (113) 703 General formula (113) Generalformula (113) CN General formula (113) General formula (113) 704 Generalformula (113) General formula (113) CN General formula (113) Generalformula (113) 705 General formula (113) General formula (113) CN Generalformula (113) General formula (113) 706 General formula (113) Generalformula (113) CN General formula (113) General formula (113) 707 Generalformula (113) General formula (113) CN General formula (113) Generalformula (113) 708 General formula (113) General formula (113) CN Generalformula (113) General formula (113) 709 General formula (113) Generalformula (113) CN General formula (113) General formula (113) 710 Generalformula (113) General formula (113) CN General formula (113) Generalformula (113) 711 General formula (113) General formula (113) CN Generalformula (113) General formula (113) 712 General formula (113) Generalformula (113) CN General formula (113) General formula (113) 713 Generalformula (113) General formula (113) CN General formula (113) Generalformula (113) 714 General formula (113) General formula (113) CN Generalformula (113) General formula (113) 715 General formula (113) Generalformula (113) CN General formula (113) General formula (113) 716 Generalformula (113) General formula (113) CN General formula (113) Generalformula (113) 717 General formula (113) General formula (113) CN Generalformula (113) General formula (113) 718 General formula (113) Generalformula (113) CN General formula (113) General formula (113) 719 Generalformula (113) General formula (113) CN General formula (113) Generalformula (113) 720 General formula (113) General formula (113) CN Generalformula (113) General formula (113) 721 General formula (113) Generalformula (113) CN General formula (113) General formula (113) 722 Generalformula (113) General formula (113) CN General formula (113) Generalformula (113) 723 General formula (113) General formula (113) CN Generalformula (113) General formula (113) 724 General formula (113) Generalformula (113) CN General formula (113) General formula (113) 725 Generalformula (113) General formula (113) CN General formula (113) Generalformula (113) 726 General formula (113) General formula (113) CN Generalformula (113) General formula (113) 727 General formula (113) Generalformula (113) CN General formula (113) General formula (113) 728 Generalformula (113) General formula (113) CN General formula (113) Generalformula (113) 729 General formula (113) General formula (113) CN Generalformula (113) General formula (113) 730 General formula (113) Generalformula (113) CN General formula (113) General formula (113) 731 Generalformula (113) General formula (113) CN General formula (113) Generalformula (113) 732 General formula (113) General formula (113) CN Generalformula (113) General formula (113) 733 General formula (113) Generalformula (113) CN General formula (113) General formula (113) 734 Generalformula (113) General formula (113) CN General formula (113) Generalformula (113) 735 General formula (113) General formula (113) CN Generalformula (113) H 736 General formula (113) General formula (113) CN HGeneral formula (113) 737 General formula (113) General formula (113) CNH H 738 General formula (113) H CN General formula (113) H 739 H Generalformula (113) CN General formula (113) H 740 General formula (113) H CNH H 741 General formula (113) General formula (113) CN General formula(113) F 742 General formula (113) General formula (113) CN F Generalformula (113) 743 General formula (113) General formula (113) CN F F 744General formula (113) F CN General formula (113) F 745 F General formula(113) CN General formula (113) F 746 General formula (113) F CN F F 747General formula (113) General formula (113) CN General formula (113) OH748 General formula (113) General formula (113) CN OH General formula(113) 749 General formula (113) General formula (113) CN OH OH 750General formula (113) OH CN General formula (113) OH 751 OH Generalformula (113) CN General formula (113) OH 752 General formula (113) OHCN OH OH 753 General formula (113) General formula (113) CN Cl Generalformula (113) 754 General formula (113) General formula (113) CN ClGeneral formula (113) 755 General formula (113) General formula (113) CNCl General formula (113) 756 General formula (113) General formula (113)CN Cl General formula (113) 757 General formula (113) General formula(113) CN Cl General formula (113) 758 General formula (113) Generalformula (113) CN Cl General formula (113) 759 General formula (113)General formula (113) CN F General formula (113) 760 General formula(113) General formula (113) CN F General formula (113) 761 Generalformula (113) General formula (113) CN F General formula (113) 762General formula (113) General formula (113) CN F General formula (113)763 General formula (113) General formula (113) CN F General formula(113) 764 General formula (113) General formula (113) CN F Generalformula (113) 765 General formula (113) General formula (113) CN CH₃OGeneral formula (113) 766 General formula (113) General formula (113) CNCH₃O General formula (113) 767 General formula (113) General formula(113) CN CH₃O General formula (113) 768 General formula (113) Generalformula (113) CN CH₃O General formula (113) 769 General formula (113)General formula (113) CN CH₃O General formula (113) 770 General formula(113) General formula (113) CN CH₃O General formula (113) 771 Generalformula (113) General formula (113) CN C₂H₅O General formula (113) 772General formula (113) General formula (113) CN C₂H₅O General formula(113) 773 General formula (113) General formula (113) CN C₂H₅O Generalformula (113) 774 General formula (113) General formula (113) CN C₂H₅OGeneral formula (113) 775 General formula (113) General formula (113) CNC₂H₅O General formula (113) 776 General formula (113) General formula(113) CN C₂H₅O General formula (113) 777 General formula (113) Generalformula (113) CN C₆H₅O General formula (113) 778 General formula (113)General formula (113) CN C₆H₅O General formula (113) 779 General formula(113) General formula (113) CN C₆H₅O General formula (113) 780 Generalformula (113) General formula (113) CN C₆H₅O General formula (113) 781General formula (113) General formula (113) CN C₆H₅O General formula(113) 782 General formula (113) General formula (113) CN C₆H₅O Generalformula (113) 783 General formula (113) General formula (113) CN Formula(121) General formula (113) 784 General formula (113) General formula(113) CN Formula (121) General formula (113) 785 General formula (113)General formula (113) CN Formula (121) General formula (113) 786 Generalformula (113) General formula (113) CN Formula (121) General formula(113) 787 General formula (113) General formula (113) CN Formula (121)General formula (113) 788 General formula (113) General formula (113) CNFormula (121) General formula (113) 789 General formula (113) Generalformula (113) CN Formula (122) General formula (113) 790 General formula(113) General formula (113) CN Formula (122) General formula (113) 791General formula (113) General formula (113) CN Formula (122) Generalformula (113) 792 General formula (113) General formula (113) CN Formula(122) General formula (113) 793 General formula (113) General formula(113) CN Formula (122) General formula (113) 794 General formula (113)General formula (113) CN Formula (122) General formula (113) 795 Generalformula (113) General formula (113) CN Formula (123) General formula(113) 796 General formula (113) General formula (113) CN Formula (123)General formula (113) 797 General formula (113) General formula (113) CNFormula (123) General formula (113) 798 General formula (113) Generalformula (113) CN Formula (123) General formula (113) 799 General formula(113) General formula (113) CN Formula (123) General formula (113) 800General formula (113) General formula (113) CN Formula (123) Generalformula (113) 801 General formula (113) General formula (113) CN Formula(124) General formula (113) 802 General formula (113) General formula(113) CN Formula (124) General formula (113) 803 General formula (113)General formula (113) CN Formula (124) General formula (113) 804 Generalformula (113) General formula (113) CN Formula (124) General formula(113) 805 General formula (113) General formula (113) CN Formula (124)General formula (113) 806 General formula (113) General formula (113) CNFormula (124) General formula (113) Compound General formula (113) No.R⁴¹ R⁴² R⁴³ R⁴⁴ R⁴⁵ R⁴⁶ 701 H H H H H H 702 H CH₃ H H H H 703 H CH₃O H HH H 704 H H CH₃ H H H 705 H H CH₃O H H H 706 H H t-C₄H₉ H H H 707 H H ClH H H 708 H H F H H H 709 H H H CH₃ H H 710 H H H CH₃O H H 711 H H H HCH₃ H 712 H H H H CH₃O H 713 H H H H t-C₄H₉ H 714 H H H H Cl H 715 H H HH F H 716 H H H H C₆H₅ H 717 H H H H p-CH₃C₆H₄ H 718 H H H H2,4,6-(CH₃)₃C₆H₂ H 719 H H H H p-CH₃OC₆H₄ H 720 H H H H p-(CH₃)₂NC₆H₄ H721 H H H H p-FC₆H₄ H 722 H H H H p-CNC₆H₄ H 723 H H H H H CH₃ 724 H H HH H CH₃O 725 H H H H H t-C₄H₉ 726 H H H H H Cl 727 H H H H H F 728 H H HH H C₆H₅ 729 H H H H H p-CH₃C₆H₄ 730 H H H H H 2,4,6-(CH₃)₃C₆H₂ 731 H HH H H p-CH₃OC₆H₄ 732 H H H H H p-(CH₃)₂NC₆H₄ 733 H H H H H p-FC₆H₄ 734 HH H H H p-CNC₆H₄ 735 H H H H H H 736 H H H H H H 737 H H H H H H 738 H HH H H H 739 H H H H H H 740 H H H H H H 741 H H H H H H 742 H H H H H H743 H H H H H H 744 H H H H H H 745 H H H H H H 746 H H H H H H 747 H HH H H H 748 H H H H H H 749 H H H H H H 750 H H H H H H 751 H H H H H H752 H H H H H H 753 H H H H H H 754 H H CH₃ H H H 755 H H CH₃O H H H 756H H t-C₄H₉ H H H 757 H H Cl H H H 758 H H F H H H 759 H H H H H H 760 HH CH₃ H H H 761 H H CH₃O H H H 762 H H t-C₄H₉ H H H 763 H H Cl H H H 764H H F H H H 765 H H H H H H 766 H H CH₃ H H H 767 H H CH₃O H H H 768 H Ht-C₄H₉ H H H 769 H H Cl H H H 770 H H F H H H 771 H H H H H H 772 H HCH₃ H H H 773 H H CH₃O H H H 774 H H t-C₄H₉ H H H 775 H H Cl H H H 776 HH F H H H 777 H H H H H H 778 H H CH₃ H H H 779 H H CH₃O H H H 780 H Ht-C₄H₉ H H H 781 H H Cl H H H 782 H H F H H H 783 H H H H H H 784 H HCH₃ H H H 785 H H CH₃O H H H 786 H H t-C₄H₉ H H H 787 H H Cl H H H 788 HH F H H H 789 H H H H H H 790 H H CH₃ H H H 791 H H CH₃O H H H 792 H Ht-C₄H₉ H H H 793 H H Cl H H H 794 H H F H H H 795 H H H H H H 796 H HCH₃ H H H 797 H H CH₃O H H H 798 H H t-C₄H₉ H H H 799 H H Cl H H H 800 HH F H H H 801 H H H H H H 802 H H CH₃ H H H 803 H H CH₃O H H H 804 H Ht-C₄H₉ H H H 805 H H Cl H H H 806 H H F H H H

TABLE 5 Compound General formula (101) No. R¹ R² R³ R⁴ R⁵ 901 Generalformula (114) General formula (114) CN General formula (114) Generalformula (114) 902 General formula (114) General formula (114) CN Generalformula (114) General formula (114) 903 General formula (114) Generalformula (114) CN General formula (114) General formula (114) 904 Generalformula (114) General formula (114) CN General formula (114) Generalformula (114) 905 General formula (114) General formula (114) CN Generalformula (114) General formula (114) 906 General formula (114) Generalformula (114) CN General formula (114) General formula (114) 907 Generalformula (114) General formula (114) CN General formula (114) Generalformula (114) 908 General formula (114) General formula (114) CN Generalformula (114) General formula (114) 909 General formula (114) Generalformula (114) CN General formula (114) General formula (114) 910 Generalformula (114) General formula (114) CN General formula (114) Generalformula (114) 911 General formula (114) General formula (114) CN Generalformula (114) General formula (114) 912 General formula (114) Generalformula (114) CN General formula (114) General formula (114) 913 Generalformula (114) General formula (114) CN General formula (114) Generalformula (114) 914 General formula (114) General formula (114) CN Generalformula (114) General formula (114) 915 General formula (114) Generalformula (114) CN General formula (114) General formula (114) 916 Generalformula (114) General formula (114) CN General formula (114) Generalformula (114) 917 General formula (114) General formula (114) CN Generalformula (114) General formula (114) 918 General formula (114) Generalformula (114) CN General formula (114) General formula (114) 919 Generalformula (114) General formula (114) CN General formula (114) H 920General formula (114) General formula (114) CN H General formula (114)921 General formula (114) General formula (114) CN H H 922 Generalformula (114) H CN General formula (114) H 923 H General formula (114)CN General formula (114) H 924 General formula (114) H CN H H 925General formula (114) General formula (114) CN General formula (114) F926 General formula (114) General formula (114) CN F General formula(114) 927 General formula (114) General formula (114) CN F F 928 Generalformula (114) F CN General formula (114) F 929 F General formula (114)CN General formula (114) F 930 General formula (114) F CN F F 931General formula (114) General formula (114) CN General formula (114) OH932 General formula (114) General formula (114) CN OH General formula(114) 933 General formula (114) General formula (114) CN OH OH 934General formula (114) OH CN General formula (114) OH 935 OH Generalformula (114) CN General formula (114) OH 936 General formula (114) OHCN OH OH 937 General formula (114) General formula (114) CN Cl Generalformula (114) 938 General formula (114) General formula (114) CN ClGeneral formula (114) 939 General formula (114) General formula (114) CNCl General formula (114) 940 General formula (114) General formula (114)CN Cl General formula (114) 941 General formula (114) General formula(114) CN Cl General formula (114) 942 General formula (114) Generalformula (114) CN Cl General formula (114) 943 General formula (114)General formula (114) CN F General formula (114) 944 General formula(114) General formula (114) CN F General formula (114) 945 Generalformula (114) General formula (114) CN F General formula (114) 946General formula (114) General formula (114) CN F General formula (114)947 General formula (114) General formula (114) CN F General formula(114) 948 General formula (114) General formula (114) CN F Generalformula (114) 949 General formula (114) General formula (114) CN CH₃OGeneral formula (114) 950 General formula (114) General formula (114) CNCH₃O General formula (114) 951 General formula (114) General formula(114) CN CH₃O General formula (114) 952 General formula (114) Generalformula (114) CN CH₃O General formula (114) 953 General formula (114)General formula (114) CN CH₃O General formula (114) 954 General formula(114) General formula (114) CN CH₃O General formula (114) 955 Generalformula (114) General formula (114) CN C₂H₅O General formula (114) 956General formula (114) General formula (114) CN C₂H₅O General formula(114) 957 General formula (114) General formula (114) CN C₂H₅O Generalformula (114) 958 General formula (114) General formula (114) CN C₂H₅OGeneral formula (114) 959 General formula (114) General formula (114) CNC₂H₅O General formula (114) 960 General formula (114) General formula(114) CN C₂H₅O General formula (114) 961 General formula (114) Generalformula (114) CN C₆H₅O General formula (114) 962 General formula (114)General formula (114) CN C₆H₅O General formula (114) 963 General formula(114) General formula (114) CN C₆H₅O General formula (114) 964 Generalformula (114) General formula (114) CN C₆H₅O General formula (114) 965General formula (114) General formula (114) CN C₆H₅O General formula(114) 966 General formula (114) General formula (114) CN C₆H₅O Generalformula (114) 967 General formula (114) General formula (114) CN Formula(121) General formula (114) 968 General formula (114) General formula(114) CN Formula (121) General formula (114) 969 General formula (114)General formula (114) CN Formula (121) General formula (114) 970 Generalformula (114) General formula (114) CN Formula (121) General formula(114) 971 General formula (114) General formula (114) CN Formula (121)General formula (114) 972 General formula (114) General formula (114) CNFormula (121) General formula (114) 973 General formula (114) Generalformula (114) CN Formula (122) General formula (114) 974 General formula(114) General formula (114) CN Formula (122) General formula (114) 975General formula (114) General formula (114) CN Formula (122) Generalformula (114) 976 General formula (114) General formula (114) CN Formula(122) General formula (114) 977 General formula (114) General formula(114) CN Formula (122) General formula (114) 978 General formula (114)General formula (114) CN Formula (122) General formula (114) 989 Generalformula (114) General formula (114) CN Formula (123) General formula(114) 980 General formula (114) General formula (114) CN Formula (123)General formula (114) 981 General formula (114) General formula (114) CNFormula (123) General formula (114) 982 General formula (114) Generalformula (114) CN Formula (123) General formula (114) 983 General formula(114) General formula (114) CN Formula (123) General formula (114) 984General formula (114) General formula (114) CN Formula (123) Generalformula (114) 985 General formula (114) General formula (114) CN Formula(124) General formula (114) 986 General formula (114) General formula(114) CN Formula (124) General formula (114) 987 General formula (114)General formula (114) CN Formula (124) General formula (114) 988 Generalformula (114) General formula (114) CN Formula (124) General formula(114) 989 General formula (114) General formula (114) CN Formula (124)General formula (114) 990 General formula (114) General formula (114) CNFormula (124) General formula (114) General formula (113) Compound R⁵¹,R⁵⁶, No. R⁵² R⁵³ R⁵⁴ R⁵⁵ R⁵⁷ R⁵⁹ R⁶¹ R⁵⁸, R⁶⁰, R⁶² 901 H H H H H H H H902 CH₃ H H H H H H H 903 CH₃O H H H H H H H 904 H CH₃ H H H H H H 905 HCH₃O H H H H H H 906 H t-C₄H₉ H H H H H H 907 H Cl H H H H H H 908 H F HH H H H H 909 H H CH₃ H H H H H 910 H H CH₃O H H H H H 911 H H H CH₃ H HH H 912 H H H CH₃O H H H H 913 H H H H CH₃ H H H 914 H H H H CH₃O H H H915 H H H H H CH₃ H H 916 H H H H H CH₃O H H 917 H H H H H H CH₃ H 918 HH H H H H CH₃O H 919 H H H H H H H H 920 H H H H H H H H 921 H H H H H HH H 922 H H H H H H H H 923 H H H H H H H H 924 H H H H H H H H 925 H HH H H H H H 926 H H H H H H H H 927 H H H H H H H H 928 H H H H H H H H929 H H H H H H H H 930 H H H H H H H H 931 H H H H H H H H 932 H H H HH H H H 933 H H H H H H H H 934 H H H H H H H H 935 H H H H H H H H 936H H H H H H H H 937 H H H H H H H H 938 H CH₃ H H H H H H 939 H CH₃O H HH H H H 940 H t-C₄H₉ H H H H H H 941 H Cl H H H H H H 942 H F H H H H HH 943 H H H H H H H H 944 H CH₃ H H H H H H 945 H CH₃O H H H H H H 946 Ht-C₄H₉ H H H H H H 947 H Cl H H H H H H 948 H F H H H H H H 949 H H H HH H H H 950 H CH₃ H H H H H H 951 H CH₃O H H H H H H 952 H t-C₄H₉ H H HH H H 953 H Cl H H H H H H 954 H F H H H H H H 955 H H H H H H H H 956 HCH₃ H H H H H H 957 H CH₃O H H H H H H 958 H t-C₄H₉ H H H H H H 959 H ClH H H H H H 960 H F H H H H H H 961 H H H H H H H H 962 H CH₃ H H H H HH 963 H CH₃O H H H H H H 964 H t-C₄H₉ H H H H H H 965 H Cl H H H H H H966 H F H H H H H H 967 H H H H H H H H 968 H CH₃ H H H H H H 969 H CH₃OH H H H H H 970 H t-C₄H₉ H H H H H H 971 H Cl H H H H H H 972 H F H H HH H H 973 H H H H H H H H 974 H CH₃ H H H H H H 975 H CH₃O H H H H H H976 H t-C₄H₉ H H H H H H 977 H Cl H H H H H H 978 H F H H H H H H 989 HH H H H H H H 980 H CH₃ H H H H H H 981 H CH₃O H H H H H H 982 H t-C₄H₉H H H H H H 983 H Cl H H H H H H 984 H F H H H H H H 985 H H H H H H H H986 H CH₃ H H H H H H 987 H CH₃O H H H H H H 988 H t-C₄H₉ H H H H H H989 H Cl H H H H H H 990 H F H H H H H H

TABLE 6 Compound General formula (101) No. R¹ R² R³ R⁴ R⁵ 1001 Generalformula (115) General formula (115) CN General formula (115) Generalformula (115) 1002 General formula (115) General formula (115) CNGeneral formula (115) General formula (115) 1003 General formula (115)General formula (115) CN General formula (115) General formula (115)1004 General formula (115) General formula (115) CN General formula(115) General formula (115) 1005 General formula (115) General formula(115) CN General formula (115) General formula (115) 1006 Generalformula (115) General formula (115) CN General formula (115) Generalformula (115) 1007 General formula (115) General formula (115) CNGeneral formula (115) General formula (115) 1008 General formula (115)General formula (115) CN General formula (115) General formula (115)1009 General formula (115) General formula (115) CN General formula(115) General formula (115) 1010 General formula (115) General formula(115) CN General formula (115) General formula (115) 1011 Generalformula (115) General formula (115) CN General formula (115) Generalformula (115) 1012 General formula (115) General formula (115) CNGeneral formula (115) General formula (115) 1013 General formula (115)General formula (115) CN General formula (115) General formula (115)1014 General formula (115) General formula (115) CN General formula(115) General formula (115) 1015 General formula (115) General formula(115) CN General formula (115) H 1016 General formula (115) Generalformula (115) CN H General formula (115) 1017 General formula (115)General formula (115) CN H H 1018 General formula (115) H CN Generalformula (115) H 1019 H General formula (115) CN General formula (115) H1020 General formula (115) H CN H H 1021 General formula (115) Generalformula (115) CN General formula (115) F 1022 General formula (115)General formula (115) CN F General formula (115) 1023 General formula(115) General formula (115) CN F F 1024 General formula (115) F CNGeneral formula (115) F 1025 F General formula (115) CN General formula(115) F 1026 General formula (115) F CN F F 1027 General formula (115)General formula (115) CN General formula (115) OH 1028 General formula(115) General formula (115) CN OH General formula (115) 1029 Generalformula (115) General formula (115) CN OH OH 1030 General formula (115)OH CN General formula (115) OH 1031 OH General formula (115) CN Generalformula (115) OH 1032 General formula (115) OH CN OH OH 1033 Generalformula (115) General formula (115) CN Cl General formula (115) 1034General formula (115) General formula (115) CN Cl General formula (115)1035 General formula (115) General formula (115) CN Cl General formula(115) 1036 General formula (115) General formula (115) CN Cl Generalformula (115) 1037 General formula (115) General formula (115) CN ClGeneral formula (115) 1038 General formula (115) General formula (115)CN Cl General formula (115) 1039 General formula (115) General formula(115) CN F General formula (115) 1040 General formula (115) Generalformula (115) CN F General formula (115) 1041 General formula (115)General formula (115) CN F General formula (115) 1042 General formula(115) General formula (115) CN F General formula (115) 1043 Generalformula (115) General formula (115) CN F General formula (115) 1044General formula (115) General formula (115) CN F General formula (115)1045 General formula (115) General formula (115) CN CH₃O General formula(115) 1046 General formula (115) General formula (115) CN CH₃O Generalformula (115) 1047 General formula (115) General formula (115) CN CH₃OGeneral formula (115) 1048 General formula (115) General formula (115)CN CH₃O General formula (115) 1049 General formula (115) General formula(115) CN CH₃O General formula (115) 1050 General formula (115) Generalformula (115) CN CH₃O General formula (115) 1051 General formula (115)General formula (115) CN C₂H₅O General formula (115) 1052 Generalformula (115) General formula (115) CN C₂H₅O General formula (115) 1053General formula (115) General formula (115) CN C₂H₅O General formula(115) 1054 General formula (115) General formula (115) CN C₂H₅O Generalformula (115) 1055 General formula (115) General formula (115) CN C₂H₅OGeneral formula (115) 1056 General formula (115) General formula (115)CN C₂H₅O General formula (115) 1057 General formula (115) Generalformula (115) CN C₆H₅O General formula (115) 1058 General formula (115)General formula (115) CN C₆H₅O General formula (115) 1059 Generalformula (115) General formula (115) CN C₆H₅O General formula (115) 1060General formula (115) General formula (115) CN C₆H₅O General formula(115) 1061 General formula (115) General formula (115) CN C₆H₅O Generalformula (115) 1062 General formula (115) General formula (115) CN C₆H₅OGeneral formula (115) 1063 General formula (115) General formula (115)CN Formula (121) General formula (115) 1064 General formula (115)General formula (115) CN Formula (121) General formula (115) 1065General formula (115) General formula (115) CN Formula (121) Generalformula (115) 1066 General formula (115) General formula (115) CNFormula (121) General formula (115) 1067 General formula (115) Generalformula (115) CN Formula (121) General formula (115) 1068 Generalformula (115) General formula (115) CN Formula (121) General formula(115) 1069 General formula (115) General formula (115) CN Formula (122)General formula (115) 1070 General formula (115) General formula (115)CN Formula (122) General formula (115) 1071 General formula (115)General formula (115) CN Formula (122) General formula (115) 1072General formula (115) General formula (115) CN Formula (122) Generalformula (115) 1073 General formula (115) General formula (115) CNFormula (122) General formula (115) 1074 General formula (115) Generalformula (115) CN Formula (122) General formula (115) 1075 Generalformula (115) General formula (115) CN Formula (123) General formula(115) 1076 General formula (115) General formula (115) CN Formula (123)General formula (115) 1077 General formula (115) General formula (115)CN Formula (123) General formula (115) 1078 General formula (115)General formula (115) CN Formula (123) General formula (115) 1079General formula (115) General formula (115) CN Formula (123) Generalformula (115) 1080 General formula (115) General formula (115) CNFormula (123) General formula (115) 1081 General formula (115) Generalformula (115) CN Formula (124) General formula (115) 1082 Generalformula (115) General formula (115) CN Formula (124) General formula(115) 1083 General formula (115) General formula (115) CN Formula (124)General formula (115) 1084 General formula (115) General formula (115)CN Formula (124) General formula (115) 1085 General formula (115)General formula (115) CN Formula (124) General formula (115) 1086General formula (115) General formula (115) CN Formula (124) Generalformula (115) Compound General formula (115) No. R⁷¹, R⁸⁰ R⁷², R⁷⁹ R⁷³,R⁷⁸ R⁷⁴, R⁷⁷ R⁷⁵, R⁷⁶ 1001 H H H H H 1002 H CH₃ H H H 1003 H CH₃O H H H1004 H C₆H₅ H H H 1005 H CH₃ H CH₃ H 1006 H CH₃O H CH₃O H 1007 H C₆H₅ HC₆H₅ H 1008 H H CH₃ H H 1009 H H CH₃O H H 1010 H H t-C₄H₉ H H 1011 H HCl H H 1012 H H F H H 1013 H H C₆H₅ H H 1014 H H p-C₆H₅—C₆H₄ H H 1015 HH H H H 1016 H H H H H 1017 H H H H H 1018 H H H H H 1019 H H H H H 1020H H H H H 1021 H H H H H 1022 H H H H H 1023 H H H H H 1024 H H H H H1025 H H H H H 1026 H H H H H 1027 H H H H H 1028 H H H H H 1029 H H H HH 1030 H H H H H 1031 H H H H H 1032 H H H H H 1033 H H H H H 1034 H HCH₃ H H 1035 H H CH₃O H H 1036 H H t-C₄H₉ H H 1037 H H Cl H H 1038 H H FH H 1039 H H H H H 1040 H H CH₃ H H 1041 H H CH₃O H H 1042 H H t-C₄H₉ HH 1043 H H Cl H H 1044 H H F H H 1045 H H H H H 1046 H H CH₃ H H 1047 HH CH₃O H H 1048 H H t-C₄H₉ H H 1049 H H Cl H H 1050 H H F H H 1051 H H HH H 1052 H H CH₃ H H 1053 H H CH₃O H H 1054 H H t-C₄H₉ H H 1055 H H Cl HH 1056 H H F H H 1057 H H H H H 1058 H H CH₃ H H 1059 H H CH₃O H H 1060H H t-C₄H₉ H H 1061 H H Cl H H 1062 H H F H H 1063 H H H H H 1064 H HCH₃ H H 1065 H H CH₃O H H 1066 H H t-C₄H₉ H H 1067 H H Cl H H 1068 H H FH H 1069 H H H H H 1070 H H CH₃ H H 1071 H H CH₃O H H 1072 H H t-C₄H₉ HH 1073 H H Cl H H 1074 H H F H H 1075 H H H H H 1076 H H CH₃ H H 1077 HH CH₃O H H 1078 H H t-C₄H₉ H H 1079 H H Cl H H 1080 H H F H H 1081 H H HH H 1082 H H CH₃ H H 1083 H H CH₃O H H 1084 H H t-C₄H₉ H H 1085 H H Cl HH 1086 H H F H H

Preferred delayed fluorescent materials include the following compounds.

[1] A compound represented by the following general formula (131):

[In the general formula (131), from 0 to 1 of R¹ to R⁵ represents acyano group, from 1 to 5 of R¹ to R⁵ each represent a group representedby the following general formula (132), and the balance of R¹ to R⁵ eachrepresent a hydrogen atom or a substituent other than the above.]

[In the general formula (132), R¹¹ to R²⁰ each independently represent ahydrogen atom or a substituent. R¹¹ and R¹², R¹² and R¹³, R¹³ and R¹⁴,R¹⁴ and R¹⁵, R¹⁵ and R¹⁶, R¹⁶ and R¹⁷, R¹⁷ and R¹⁸, R¹⁸ and R¹⁹, and R¹⁹and R²⁰ each may be bonded to each other to form a cyclic structure. L¹²represents a substituted or unsubstituted arylene group or a substitutedor unsubstituted heteroarylene group.][2] The compound according to [1], wherein the group represented by thegeneral formula (132) is a group represented by any one of the followinggeneral formulae (133) to (138):

[In the general formulae (133) to (138), R²¹ to R²⁴, R²⁷ to R³⁸, R⁴¹ toR⁴⁸, R⁵¹ to R⁵⁸, R⁶¹ to R⁶⁵, R⁷¹ to R⁷⁹, R⁸¹ to R⁹⁰ each independentlyrepresent a hydrogen atom or a substituent. R²¹ and R²², R²² and R²³,R²³ and R²⁴, R²⁷ and R²⁸, R⁸ and R⁹, R²⁹ and R³⁰, R³¹ and R³², R³² andR³³, R³³ and R³⁴, R³⁵ and R³⁶, R³⁶ and R³⁷, R³⁷ and R³⁸, R⁴¹ and R⁴²,R⁴² and R⁴³, R⁴³ and R⁴⁴, R⁴⁵ and R⁴⁶, R⁴⁶ and R⁴⁷, R⁴⁷ and R⁴⁸, R⁵¹ andR⁵², R⁵² and R⁵³, R⁵³ and R⁵⁴, R⁵⁵ and R⁵⁶, R⁵⁶ and R⁵⁷, R⁵⁷ and R⁵⁸,R⁶¹ and R⁶², R⁶² and R⁶³, R⁶³ and R⁶⁴, R⁶⁴ and R⁶⁵, R⁵⁴ and R⁶¹, R⁵⁵ andR⁶⁵, R⁷¹ and R⁷², R⁷² and R⁷³, R⁷³ and R⁷⁴, R⁷⁴ and R⁷⁵, R⁷⁶ and R⁷⁷,R⁷⁷ and R⁷⁸, R⁷⁸ and R⁷⁹, R⁸¹ and R⁸², R⁸² and R⁸³, R⁸³ and R⁸⁴, R⁸⁵ andR⁸⁶, R⁸⁶ and R⁸⁷, R⁸⁷ and R⁸⁸, and R⁸⁹ and R⁹⁰ each may be bonded toeach other to form a cyclic structure. L¹³ to L¹⁸ each independentlyrepresent a substituted or unsubstituted arylene group or a substitutedor unsubstituted heteroarylene group.][3] The compound according to [1] or [2], wherein in the general formula(131), R³ represents a cyano group.[4] The compound according to any one of [1] to [3], wherein in thegeneral formula (131), R¹ and R⁴ each represent a group represented bythe general formula (132).[5] The compound according to any one of [1] to [4], wherein in thegeneral formula (132), L¹² represents a phenylene group.[6] The compound according to any one of [1] to [5], wherein the grouprepresented by the general formula (132) is a group represented by thegeneral formula (133).[7] The compound according to [6], wherein in the general formula (133),L¹³ represents a 1,3-phenylene group.[8] The compound according to any one of [1] to [5], wherein the grouprepresented by the general formula (132) is a group represented by thegeneral formula (134).[9] The compound according to [8], wherein in the general formula (134),L¹⁴ represents a 1,4-phenylene group.[10] The compound according to any one of [1] to [5], wherein the grouprepresented by the general formula (132) is a group represented by thegeneral formula (138).[11] The compound according to [10], wherein in the general formula(132), L¹⁸ represents a 1,4-phenylene group.

Examples of the compound include the following compounds.

Examples of the preferred delayed fluorescent material include compoundsrepresented by the following general formula. The entire description ofWO 2013/011954 including the paragraphs 0007 to 0047 and 0073 to 0085 isincorporated herein by reference as a part of the description of thepresent application.

[In the general formula (141), R¹, R², R³, R⁴, R⁵, R⁶, R⁷, R⁸ and R¹⁷each independently represent a hydrogen atom or an electron donatinggroup, provided that at least one thereof represents an electrondonating group. R⁹, R¹⁰, R¹¹, R¹², R¹³, R¹⁴, R¹⁵ and R¹⁶ eachindependently represent a hydrogen atom or an electron withdrawing grouphaving no unshared electron pair at the α-position. Z represents asingle bond or >C═Y, wherein Y represents O, S, C(CN)₂ or C(COOH)₂,provided that when Z represents a single bond, at least one of R⁹, R¹⁰,R¹¹, R¹², R¹³, R¹⁴, R¹⁵ and R¹⁶ represents an electron withdrawing grouphaving no unshared electron pair at the α-position.

Specific examples of the compounds include the compounds shown in thefollowing Table 7 to Table 16. In the Tables, D1 to D3 represent thefollowing aryl groups substituted by an electron donating group,respectively; A1 to A5 represent the following electron withdrawinggroups, respectively; H represents a hydrogen atom; and Ph represents aphenyl group.

TABLE 7 Compound No. R² R⁷ R¹⁰ R¹⁵ R¹⁷ Z Other Rs 2001 H H A1 A1 Phsingle bond H 2002 H D1 A1 A1 Ph single bond H 2003 H D2 A1 A1 Ph singlebond H 2004 H D3 A1 A1 Ph single bond H 2005 H H A2 A2 Ph single bond H2006 H D1 A2 A2 Ph single bond H 2007 H D2 A2 A2 Ph single bond H 2008 HD3 A2 A2 Ph single bond H 2009 H H A3 A3 Ph single bond H 2010 H D1 A3A3 Ph single bond H 2011 H D2 A3 A3 Ph single bond H 2012 H D3 A3 A3 Phsingle bond H 2013 H H A4 A4 Ph single bond H 2014 H D1 A4 A4 Ph singlebond H 2015 H D2 A4 A4 Ph single bond H 2016 H D3 A4 A4 Ph single bond H2017 H H A5 A5 Ph single bond H 2018 H D1 A5 A5 Ph single bond H 2019 HD2 A5 A5 Ph single bond H 2020 H D3 A5 A5 Ph single bond H 2021 D1 D1 A1A1 Ph single bond H 2022 D2 D2 A1 A1 Ph single bond H 2023 D3 D3 A1 A1Ph single bond H 2024 D1 D1 A2 A2 Ph single bond H 2025 D2 D2 A2 A2 Phsingle bond H 2026 D3 D3 A2 A2 Ph single bond H 2027 D1 D1 A3 A3 Phsingle bond H 2028 D2 D2 A3 A3 Ph single bond H 2029 D3 D3 A3 A3 Phsingle bond H 2030 D1 D1 A4 A4 Ph single bond H 2031 D2 D2 A4 A4 Phsingle bond H 2032 D3 D3 A4 A4 Ph single bond H 2033 D1 D1 A5 A5 Phsingle bond H 2034 D2 D2 A5 A5 Ph single bond H 2035 D3 D3 A5 A5 Phsingle bond H

TABLE 8 Compound No. R³ R⁶ R¹¹ R¹⁴ R¹⁷ Z Other Rs 2036 H H H A1 Phsingle bond H 2037 H D1 H A1 Ph single bond H 2038 H D2 H A1 Ph singlebond H 2039 H D3 H A1 Ph single bond H 2040 H H H A2 Ph single bond H2041 H D1 H A2 Ph single bond H 2042 H D2 H A2 Ph single bond H 2043 HD3 H A2 Ph single bond H 2044 H H H A3 Ph single bond H 2045 H D1 H A3Ph single bond H 2046 H D2 H A3 Ph single bond H 2047 H D3 H A3 Phsingle bond H 2048 H H H A4 Ph single bond H 2049 H D1 H A4 Ph singlebond H 2050 H D2 H A4 Ph single bond H 2051 H D3 H A4 Ph single bond H2052 H H H A5 Ph single bond H 2053 H D1 H A5 Ph single bond H 2054 H D2H A5 Ph single bond H 2055 H D3 H A5 Ph single bond H 2056 D1 D1 H A1 Phsingle bond H 2057 D2 D2 H A1 Ph single bond H 2058 D3 D3 H A1 Ph singlebond H 2059 D1 D1 H A2 Ph single bond H 2060 D2 D2 H A2 Ph single bond H2061 D3 D3 H A2 Ph single bond H 2062 D1 D1 H A3 Ph single bond H 2063D2 D2 H A3 Ph single bond H 2064 D3 D3 H A3 Ph single bond H 2065 D1 D1H A4 Ph single bond H 2066 D2 D2 H A4 Ph single bond H 2067 D3 D3 H A4Ph single bond H 2068 D1 D1 H A5 Ph single bond H 2069 D2 D2 H A5 Phsingle bond H 2070 D3 D3 H A5 Ph single bond H

TABLE 9 Compound No. R² R⁷ R¹⁰ R¹⁵ R¹⁷ Z Other Rs 2071 H H A1 A1 Ph C═OH 2072 H D1 A1 A1 Ph C═O H 2073 H D2 A1 A1 Ph C═O H 2074 H D3 A1 A1 PhC═O H 2075 H H A2 A2 Ph C═O H 2076 H D1 A2 A2 Ph C═O H 2077 H D2 A2 A2Ph C═O H 2078 H D3 A2 A2 Ph C═O H 2079 H H A3 A3 Ph C═O H 2080 H D1 A3A3 Ph C═O H 2081 H D2 A3 A3 Ph C═O H 2082 H D3 A3 A3 Ph C═O H 2083 H HA4 A4 Ph C═O H 2084 H D1 A4 A4 Ph C═O H 2085 H D2 A4 A4 Ph C═O H 2086 HD3 A4 A4 Ph C═O H 2087 H H A5 A5 Ph C═O H 2088 H D1 A5 A5 Ph C═O H 2089H D2 A5 A5 Ph C═O H 2090 H D3 A5 A5 Ph C═O H 2091 D1 D1 A1 A1 Ph C═O H2092 D2 D2 A1 A1 Ph C═O H 2093 D3 D3 A1 A1 Ph C═O H 2094 D1 D1 A2 A2 PhC═O H 2095 D2 D2 A2 A2 Ph C═O H 2096 D3 D3 A2 A2 Ph C═O H 2097 D1 D1 A3A3 Ph C═O H 2098 D2 D2 A3 A3 Ph C═O H 2099 D3 D3 A3 A3 Ph C═O H 2100 D1D1 A4 A4 Ph C═O H 2101 D2 D2 A4 A4 Ph C═O H 2102 D3 D3 A4 A4 Ph C═O H2103 D1 D1 A5 A5 Ph C═O H 2104 D2 D2 A5 A5 Ph C═O H 2105 D3 D3 A5 A5 PhC═O H

TABLE 10 Compound No. R³ R⁶ R¹¹ R¹⁴ R¹⁷ Z Other Rs 2106 H H H A1 Ph C═OH 2107 H D1 H A1 Ph C═O H 2108 H D2 H A1 Ph C═O H 2109 H D3 H A1 Ph C═OH 2110 H H H A2 Ph C═O H 2111 H D1 H A2 Ph C═O H 2112 H D2 H A2 Ph C═O H2113 H D3 H A2 Ph C═O H 2114 H H H A3 Ph C═O H 2115 H D1 H A3 Ph C═O H2116 H D2 H A3 Ph C═O H 2117 H D3 H A3 Ph C═O H 2118 H H H A4 Ph C═O H2119 H D1 H A4 Ph C═O H 2120 H D2 H A4 Ph C═O H 2121 H D3 H A4 Ph C═O H2122 H H H A5 Ph C═O H 2123 H D1 H A5 Ph C═O H 2124 H D2 H A5 Ph C═O H2125 H D3 H A5 Ph C═O H 2126 D1 D1 H A1 Ph C═O H 2127 D2 D2 H A1 Ph C═OH 2128 D3 D3 H A1 Ph C═O H 2129 D1 D1 H A2 Ph C═O H 2130 D2 D2 H A2 PhC═O H 2131 D3 D3 H A2 Ph C═O H 2132 D1 D1 H A3 Ph C═O H 2133 D2 D2 H A3Ph C═O H 2134 D3 D3 H A3 Ph C═O H 2135 D1 D1 H A4 Ph C═O H 2136 D2 D2 HA4 Ph C═O H 2137 D3 D3 H A4 Ph C═O H 2138 D1 D1 H A5 Ph C═O H 2139 D2 D2H A5 Ph C═O H 2140 D3 D3 H A5 Ph C═O H 2141 H H H H Ph C═O H

TABLE 11 Compound No. R² R⁷ R¹⁰ R¹⁵ R¹⁷ Z Other Rs 2142 H H A1 A1 Ph C═SH 2143 H D1 A1 A1 Ph C═S H 2144 H D2 A1 A1 Ph C═S H 2145 H D3 A1 A1 PhC═S H 2146 H H A2 A2 Ph C═S H 2147 H D1 A2 A2 Ph C═S H 2148 H D2 A2 A2Ph C═S H 2149 H D3 A2 A2 Ph C═S H 2150 H H A3 A3 Ph C═S H 2151 H D1 A3A3 Ph C═S H 2152 H D2 A3 A3 Ph C═S H 2153 H D3 A3 A3 Ph C═S H 2154 H HA4 A4 Ph C═S H 2155 H D1 A4 A4 Ph C═S H 2156 H D2 A4 A4 Ph C═S H 2157 HD3 A4 A4 Ph C═S H 2158 H H A5 A5 Ph C═S H 2159 H D1 A5 A5 Ph C═S H 2160H D2 A5 A5 Ph C═S H 2161 H D3 A5 A5 Ph C═S H 2162 D1 D1 A1 A1 Ph C═S H2163 D2 D2 A1 A1 Ph C═S H 2164 D3 D3 A1 A1 Ph C═S H 2165 D1 D1 A2 A2 PhC═S H 2166 D2 D2 A2 A2 Ph C═S H 2167 D3 D3 A2 A2 Ph C═S H 2168 D1 D1 A3A3 Ph C═S H 2169 D2 D2 A3 A3 Ph C═S H 2170 D3 D3 A3 A3 Ph C═S H 2171 D1D1 A4 A4 Ph C═S H 2172 D2 D2 A4 A4 Ph C═S H 2173 D3 D3 A4 A4 Ph C═S H2174 D1 D1 A5 A5 Ph C═S H 2175 D2 D2 A5 A5 Ph C═S H 2176 D3 D3 A5 A5 PhC═S H

TABLE 12 Compound No. R³ R⁶ R¹¹ R¹⁴ R¹⁷ Z Other Rs 2177 H H H A1 Ph C═SH 2178 H D1 H A1 Ph C═S H 2179 H D2 H A1 Ph C═S H 2180 H D3 H A1 Ph C═SH 2181 H H H A2 Ph C═S H 2182 H D1 H A2 Ph C═S H 2183 H D2 H A2 Ph C═S H2184 H D3 H A2 Ph C═S H 2185 H H H A3 Ph C═S H 2186 H D1 H A3 Ph C═S H2187 H D2 H A3 Ph C═S H 2188 H D3 H A3 Ph C═S H 2189 H H H A4 Ph C═S H2190 H D1 H A4 Ph C═S H 2191 H D2 H A4 Ph C═S H 2192 H D3 H A4 Ph C═S H2193 H H H A5 Ph C═S H 2194 H D1 H A5 Ph C═S H 2195 H D2 H A5 Ph C═S H2196 H D3 H A5 Ph C═S H 2197 D1 D1 H A1 Ph C═S H 2198 D2 D2 H A1 Ph C═SH 2199 D3 D3 H A1 Ph C═S H 2200 D1 D1 H A2 Ph C═S H 2201 D2 D2 H A2 PhC═S H 2202 D3 D3 H A2 Ph C═S H 2203 D1 D1 H A3 Ph C═S H 2204 D2 D2 H A3Ph C═S H 2205 D3 D3 H A3 Ph C═S H 2206 D1 D1 H A4 Ph C═S H 2207 D2 D2 HA4 Ph C═S H 2208 D3 D3 H A4 Ph C═S H 2209 D1 D1 H A5 Ph C═S H 2210 D2 D2H A5 Ph C═S H 2211 D3 D3 H A5 Ph C═S H 2212 H H H H Ph C═S H

TABLE 13 Compound No. R² R⁷ R¹⁰ R¹⁵ R¹⁷ Z Other Rs 2213 H H A1 A1 PhC═C(CN)₂ H 2214 H D1 A1 A1 Ph C═C(CN)₂ H 2215 H D2 A1 A1 Ph C═C(CN)₂ H2216 H D3 A1 A1 Ph C═C(CN)₂ H 2217 H H A2 A2 Ph C═C(CN)₂ H 2218 H D1 A2A2 Ph C═C(CN)₂ H 2219 H D2 A2 A2 Ph C═C(CN)₂ H 2220 H D3 A2 A2 PhC═C(CN)₂ H 2221 H H A3 A3 Ph C═C(CN)₂ H 2222 H D1 A3 A3 Ph C═C(CN)₂ H2223 H D2 A3 A3 Ph C═C(CN)₂ H 2224 H D3 A3 A3 Ph C═C(CN)₂ H 2225 H H A4A4 Ph C═C(CN)₂ H 2226 H D1 A4 A4 Ph C═C(CN)₂ H 2227 H D2 A4 A4 PhC═C(CN)₂ H 2228 H D3 A4 A4 Ph C═C(CN)₂ H 2229 H H A5 A5 Ph C═C(CN)₂ H2230 H D1 A5 A5 Ph C═C(CN)₂ H 2231 H D2 A5 A5 Ph C═C(CN)₂ H 2232 H D3 A5A5 Ph C═C(CN)₂ H 2233 D1 D1 A1 A1 Ph C═C(CN)₂ H 2234 D2 D2 A1 A1 PhC═C(CN)₂ H 2235 D3 D3 A1 A1 Ph C═C(CN)₂ H 2236 D1 D1 A2 A2 Ph C═C(CN)₂ H2237 D2 D2 A2 A2 Ph C═C(CN)₂ H 2238 D3 D3 A2 A2 Ph C═C(CN)₂ H 2239 D1 D1A3 A3 Ph C═C(CN)₂ H 2240 D2 D2 A3 A3 Ph C═C(CN)₂ H 2241 D3 D3 A3 A3 PhC═C(CN)₂ H 2242 D1 D1 A4 A4 Ph C═C(CN)₂ H 2243 D2 D2 A4 A4 Ph C═C(CN)₂ H2244 D3 D3 A4 A4 Ph C═C(CN)₂ H 2245 D1 D1 A5 A5 Ph C═C(CN)₂ H 2246 D2 D2A5 A5 Ph C═C(CN)₂ H 2247 D3 D3 A5 A5 Ph C═C(CN)₂ H

TABLE 14 Compound No. R³ R⁶ R¹¹ R¹⁴ R¹⁷ Z Other Rs 2248 H H H A1 PhC═C(CN)₂ H 2249 H D1 H A1 Ph C═C(CN)₂ H 2250 H D2 H A1 Ph C═C(CN)₂ H2251 H D3 H A1 Ph C═C(CN)₂ H 2252 H H H A2 Ph C═C(CN)₂ H 2253 H D1 H A2Ph C═C(CN)₂ H 2254 H D2 H A2 Ph C═C(CN)₂ H 2255 H D3 H A2 Ph C═C(CN)₂ H2256 H H H A3 Ph C═C(CN)₂ H 2257 H D1 H A3 Ph C═C(CN)₂ H 2258 H D2 H A3Ph C═C(CN)₂ H 2259 H D3 H A3 Ph C═C(CN)₂ H 2260 H H H A4 Ph C═C(CN)₂ H2261 H D1 H A4 Ph C═C(CN)₂ H 2262 H D2 H A4 Ph C═C(CN)₂ H 2263 H D3 H A4Ph C═C(CN)₂ H 2264 H H H A5 Ph C═C(CN)₂ H 2265 H D1 H A5 Ph C═C(CN)₂ H2266 H D2 H A5 Ph C═C(CN)₂ H 2267 H D3 H A5 Ph C═C(CN)₂ H 2268 D1 D1 HA1 Ph C═C(CN)₂ H 2269 D2 D2 H A1 Ph C═C(CN)₂ H 2270 D3 D3 H A1 PhC═C(CN)₂ H 2271 D1 D1 H A2 Ph C═C(CN)₂ H 2272 D2 D2 H A2 Ph C═C(CN)₂ H2273 D3 D3 H A2 Ph C═C(CN)₂ H 2274 D1 D1 H A3 Ph C═C(CN)₂ H 2275 D2 D2 HA3 Ph C═C(CN)₂ H 2276 D3 D3 H A3 Ph C═C(CN)₂ H 2277 D1 D1 H A4 PhC═C(CN)₂ H 2278 D2 D2 H A4 Ph C═C(CN)₂ H 2279 D3 D3 H A4 Ph C═C(CN)₂ H2280 D1 D1 H A5 Ph C═C(CN)₂ H 2281 D2 D2 H A5 Ph C═C(CN)₂ H 2282 D3 D3 HA5 Ph C═C(CN)₂ H 2283 H H H H Ph C═C(CN)₂ H

TABLE 15 Compound No. R² R⁷ R¹⁰ R¹⁵ R¹⁷ Z Other Rs 2284 H H A1 A1 PhC═C(COOH)₂ H 2285 H D1 A1 A1 Ph C═C(COOH)₂ H 2286 H D2 A1 A1 PhC═C(COOH)₂ H 2287 H D3 A1 A1 Ph C═C(COOH)₂ H 2288 H H A2 A2 PhC═C(COOH)₂ H 2289 H D1 A2 A2 Ph C═C(COOH)₂ H 2290 H D2 A2 A2 PhC═C(COOH)₂ H 2291 H D3 A2 A2 Ph C═C(COOH)₂ H 2292 H H A3 A3 PhC═C(COOH)₂ H 2293 H D1 A3 A3 Ph C═C(COOH)₂ H 2294 H D2 A3 A3 PhC═C(COOH)₂ H 2295 H D3 A3 A3 Ph C═C(COOH)₂ H 2296 H H A4 A4 PhC═C(COOH)₂ H 2297 H D1 A4 A4 Ph C═C(COOH)₂ H 2298 H D2 A4 A4 PhC═C(COOH)₂ H 2299 H D3 A4 A4 Ph C═C(COOH)₂ H 2300 H H A5 A5 PhC═C(COOH)₂ H 2301 H D1 A5 A5 Ph C═C(COOH)₂ H 2302 H D2 A5 A5 PhC═C(COOH)₂ H 2303 H D3 A5 A5 Ph C═C(COOH)₂ H 2304 D1 D1 A1 A1 PhC═C(COOH)₂ H 2305 D2 D2 A1 A1 Ph C═C(COOH)₂ H 2306 D3 D3 A1 A1 PhC═C(COOH)₂ H 2307 D1 D1 A2 A2 Ph C═C(COOH)₂ H 2308 D2 D2 A2 A2 PhC═C(COOH)₂ H 2309 D3 D3 A2 A2 Ph C═C(COOH)₂ H 2310 D1 D1 A3 A3 PhC═C(COOH)₂ H 2311 D2 D2 A3 A3 Ph C═C(COOH)₂ H 2312 D3 D3 A3 A3 PhC═C(COOH)₂ H 2313 D1 D1 A4 A4 Ph C═C(COOH)₂ H 2314 D2 D2 A4 A4 PhC═C(COOH)₂ H 2315 D3 D3 A4 A4 Ph C═C(COOH)₂ H 2316 D1 D1 A5 A5 PhC═C(COOH)₂ H 2317 D2 D2 A5 A5 Ph C═C(COOH)₂ H 2318 D3 D3 A5 A5 PhC═C(COOH)₂ H

TABLE 16 Compound No. R³ R⁶ R¹¹ R¹⁴ R¹⁷ Z Other Rs 2319 H H H A1 PhC═C(COOH)₂ H 2320 H D1 H A1 Ph C═C(COOH)₂ H 2321 H D2 H A1 Ph C═C(COOH)₂H 2322 H D3 H A1 Ph C═C(COOH)₂ H 2323 H H H A2 Ph C═C(COOH)₂ H 2324 H D1H A2 Ph C═C(COOH)₂ H 2325 H D2 H A2 Ph C═C(COOH)₂ H 2326 H D3 H A2 PhC═C(COOH)₂ H 2327 H H H A3 Ph C═C(COOH)₂ H 2328 H D1 H A3 Ph C═C(COOH)₂H 2329 H D2 H A3 Ph C═C(COOH)₂ H 2330 H D3 H A3 Ph C═C(COOH)₂ H 2331 H HH A4 Ph C═C(COOH)₂ H 2332 H D1 H A4 Ph C═C(COOH)₂ H 2333 H D2 H A4 PhC═C(COOH)₂ H 2334 H D3 H A4 Ph C═C(COOH)₂ H 2335 H H H A5 Ph C═C(COOH)₂H 2336 H D1 H A5 Ph C═C(COOH)₂ H 2337 H D2 H A5 Ph C═C(COOH)₂ H 2338 HD3 H A5 Ph C═C(COOH)₂ H 2339 D1 D1 H A1 Ph C═C(COOH)₂ H 2340 D2 D2 H A1Ph C═C(COOH)₂ H 2341 D3 D3 H A1 Ph C═C(COOH)₂ H 2342 D1 D1 H A2 PhC═C(COOH)₂ H 2343 D2 D2 H A2 Ph C═C(COOH)₂ H 2344 D3 D3 H A2 PhC═C(COOH)₂ H 2345 D1 D1 H A3 Ph C═C(COOH)₂ H 2346 D2 D2 H A3 PhC═C(COOH)₂ H 2347 D3 D3 H A3 Ph C═C(COOH)₂ H 2348 D1 D1 H A4 PhC═C(COOH)₂ H 2349 D2 D2 H A4 Ph C═C(COOH)₂ H 2350 D3 D3 H A4 PhC═C(COOH)₂ H 2351 D1 D1 H A5 Ph C═C(COOH)₂ H 2352 D2 D2 H A5 PhC═C(COOH)₂ H 2353 D3 D3 H A5 Ph C═C(COOH)₂ H 2354 H H H H Ph C═C(COOH)₂H

Examples of the preferred delayed fluorescent material include compoundsrepresented by the following general formula. The entire description ofWO 2013/011955 including the paragraphs 0007 to 0033 and 0059 to 0066 isincorporated herein by reference as a part of the description of thepresent application.

[In the general formula (151), R¹, R², R³, R⁴, R⁵, R⁶, R⁷ and R⁸ eachindependently represent a hydrogen atom or an electron donating group,provided that at least one thereof represents an electron donatinggroup. R⁹, R¹⁰, R¹, R¹², R¹³, R¹⁴, R¹⁵ and R¹⁶ each independentlyrepresent a hydrogen atom or an electron withdrawing group, providedthat at least one thereof represents an electron withdrawing group.]

Specific examples of the compounds include the compounds shown in thefollowing Table 17 to Table 20. In the Tables, D11 to D20 represent theunsubstituted electron donating groups having the following structures,respectively.

TABLE 17 Compound No. R² R⁷ R¹⁰ R¹⁵ Other Rs 3002 D11 D11 CN CN H 3003D12 D12 CN CN H 3004 D13 D13 CN CN H 3005 D14 D14 CN CN H 3006 D15 D15CN CN H 3007 D16 D16 CN CN H 3008 D17 D17 CN CN H 3009 D18 D18 CN CN H3010 D19 D19 CN CN H 3011 D20 D20 CN CN H 3012 H D11 H CN H 3013 H D12 HCN H 3014 H D13 H CN H 3015 H D14 H CN H 3016 H D15 H CN H 3017 H D16 HCN H 3018 H D17 H CN H 3019 H D18 H CN H 3020 H D19 H CN H 3021 H D20 HCN H

TABLE 18 Compound No. R³ R⁶ R¹¹ R¹⁴ Other Rs 3022 D11 D11 CN CN H 3023D12 D12 CN CN H 3024 D13 D13 CN CN H 3025 D14 D14 CN CN H 3026 D15 D15CN CN H 3027 D16 D16 CN CN H 3028 D17 D17 CN CN H 3029 D18 D18 CN CN H3030 D19 D19 CN CN H 3031 D20 D20 CN CN H 3032 H D11 H CN H 3033 H D12 HCN H 3034 H D13 H CN H 3035 H D14 H CN H 3036 H D15 H CN H 3037 H D16 HCN H 3038 H D17 H CN H 3039 H D18 H CN H 3040 H D19 H CN H 3041 H D20 HCN H

TABLE 19 Compound No. R², R⁷ R³, R⁶ R¹⁰, R¹⁵ R¹¹, R¹⁴ Other Rs 3042diphenylamino group H CN H H 3043 bis(2-methylphenyl)amino group H CN HH 3044 bis(3-methylphenyl)amino group H CN H H 3045bis(2,4-dimethylphenyl)amino group H CN H H 3046bis(2,6-dimethylphenyl)amino group H CN H H 3047bis(3,5-dimethylphenyl)amino group H CN H H 3048bis(2,4,6-trimethylphenyl)amino group H CN H H 3049bis(4-ethylphenyl)amino group H CN H H 3050 bis(4-propylphenyl)aminogroup H CN H H 3051 diphenylamino group H H CN H 3052bis(2-methylphenyl)amino group H H CN H 3053 bis(3-methylphenyl)aminogroup H H CN H 3054 bis(4-methylphenyl)amino group H H CN H 3055bis(2,4-dimethylphenyl)amino group H H CN H 3056bis(2,6-dimethylphenyl)amino group H H CN H 3057bis(3,5-dimethylphenyl)amino group H H CN H 3058bis(2,4,6-trimethylphenyl)amino group H H CN H 3059bis(4-ethylphenyl)amino group H H CN H 3060 bis(4-propylphenyl)aminogroup H H CN H

TABLE 20 Compound No. R², R⁷ R³, R⁶ R¹⁰, R¹⁵ R¹¹, R¹⁴ Other Rs 3061 Hdiphenylamino group CN H H 3062 H bis(2-methylphenyl)amino group CN H H3063 H bis(3-methylphenyl)amino group CN H H 3064 Hbis(4-methylphenyl)amino group CN H H 3065 Hbis(2,4-dimethylphenyl)amino group CN H H 3066 Hbis(2,6-dimethylphenyl)amino group CN H H 3067 Hbis(3,5-dimethylphenyl)amino group CN H H 3068 Hbis(2,4,6-trimethylphenyl)amino group CN H H 3069 Hbis(4-ethylphenyl)amino group CN H H 3070 H bis(4-propylphenyl)aminogroup CN H H 3071 H diphenylamino group H CN H 3072 Hbis(2-methylphenyl)amino group H CN H 3073 H bis(3-methylphenyl)aminogroup H CN H 3074 H bis(4-methylphenyl)amino group H CN H 3075 Hbis(2,4-dimethylphenyl)amino group H CN H 3076 Hbis(2,6-dimethylphenyl)amino group H CN H 3077 Hbis(3,5-dimethylphenyl)amino group H CN H 3078 Hbis(2,4,6-trimethylphenyl)amino group H CN H 3079 Hbis(4-ethylphenyl)amino group H CN H 3080 H bis(4-propylphenyl)aminogroup H CN H

Examples of the preferred delayed fluorescent material include compoundsrepresented by the following general formula. The entire description ofWO 2013/081088 including the paragraphs 0008 to 0071 and 0118 to 0133 isincorporated herein by reference as a part of the description of thepresent application.

[In the general formula (161), any two of Y¹, Y² and Y³ each represent anitrogen atom, and the balance thereof represents a methine group, ofall Y¹, Y² and Y³ each represent a nitrogen atom. Z¹ and Z² eachindependently represent a hydrogen atom or a substituent. R¹ to R⁸ eachindependently represent a hydrogen atom or a substituent, provided thatat least one of R¹ to R⁸ represents a substituted or unsubstituteddiarylamino group or a substituted or unsubstituted carbazolyl group.The compound represented by the general formula (161) has at least twocarbazole structures in the molecule thereof.

Examples of the compound include the following compounds.

Examples of the preferred delayed fluorescent material include compoundsrepresented by the following general formula. The entire description ofJP-A-2013-256490 including the paragraphs 0009 to 0046 and 0093 to 0134is incorporated herein by reference as a part of the description of thepresent application.

[In the general formula (171), Ar¹ to Ar³ each independently represent asubstituted or unsubstituted aryl group, and at least one of themrepresents a substituted aryl group represented by the following generalformula (172).]

[In the general formula (172), R¹ to R⁸ each independently represent ahydrogen atom or a substituent. Z represents O, S, O═C or Ar⁴—N, Ar⁴represents a substituted or unsubstituted aryl group. R¹ and R², R² andR³, R³ and R⁴, R⁵ and R⁶, R⁶ and R⁷, and R⁷ and R⁸ each independentlymay be bonded to each other to form a cyclic structure.]

Examples of the compound include the following compounds.

Examples of the preferred delayed fluorescent material include compoundsrepresented by the following general formula. The entire description ofJP-A-2013-116975 including the paragraphs 0008 to 0020 and 0038 to 0040is incorporated herein by reference as a part of the description of thepresent application.

[In the general formula (R¹, R², R⁴ to R⁸, R¹¹, R¹² and R¹⁴ to R¹⁸ eachindependently represent a hydrogen atom or a substituent.]

Examples of the preferred delayed fluorescent material include thefollowing compounds.

[1] A compound represented by the following general formula (191):

[In the general formula (191), Ar¹ represents a substituted orunsubstituted arylene group; Ar² and Ar³ each independently represent asubstituted or unsubstituted aryl group. R¹ to R⁸ each independentlyrepresent a hydrogen atom or a substituent, provided that at least oneof R¹ to R⁸ represents a substituted or unsubstituted diarylamino group,and R¹ and R², R² and R³, R³ and R⁴, R⁵ and R⁶, R⁶ and R⁷, and R⁷ and R⁸each may be bonded to each other to form a cyclic structure.[2] The compound according to [1], wherein in the general formula (191),at least one of R¹ to R⁴ represents a substituted or unsubstituteddiarylamino group, and at least one of R⁵ to R⁸ represents a substitutedor unsubstituted diarylamino group.[3] The compound according to [2], wherein in the general formula (191),R³ and R⁶ each represent a substituted or unsubstituted diarylaminogroup.[4] The compound according to any one of [1] to [3], wherein in thegeneral formula (191), at least one of R¹ to R⁸ represents a substitutedor unsubstituted diphenylamino group.[5] The compound according to any one of [1] to [4], wherein in thegeneral formula (191), Ar² and Ar³ each independently represent asubstituted or unsubstituted phenyl group.[6] The compound according to any one of [1] to [5], wherein in thegeneral formula (191), Ar¹ each independently represents a substitutedor unsubstituted phenylene group, a substituted or unsubstitutednaphthylene group or a substituted or unsubstituted anthracenylenegroup.[7] The compound according to [1], wherein the compound has a structurerepresented by the following general formula (192):

[In the general formula (192), R¹ to R⁸ and R¹¹ to R²⁴ eachindependently represent a hydrogen atom or a substituent, provided thatat least one of R¹ to R⁸ represents a substituted or unsubstituteddiarylamino group, and R¹ and R², R² and R³, R³ and R⁴, R⁵ and R⁶, R⁶and R⁷, R⁷ and R⁸, R¹¹ and R¹²; R¹² and R¹³, R¹³ and R¹⁴, R¹⁴ and R¹⁵,R¹⁶ and R¹⁷, R¹⁷ and R¹⁸, R¹⁸ and R¹⁹, R¹⁹ and R²⁰, R²¹ and R²², and R²³and R²⁴ each may be bonded to each other to form a cyclic structure.][8] The compound according to [7], wherein in the general formula (192),at least one of R¹ to R⁴ represents a substituted or unsubstituteddiarylamino group, and at least one of R⁵ to R⁸ represents a substitutedor unsubstituted diarylamino group.[9] The compound according to [8], wherein in the general formula (192),R³ and R⁶ each represent a substituted or unsubstituted diarylaminogroup.

Specific examples of the compound include the following compounds. Phrepresents a phenyl group.

Examples of the preferred delayed fluorescent material include thefollowing compounds.

[1] A compound represented by the following general formula (201):

(In the above formula, R¹ to R⁸ each independently represent a hydrogenatom or a substituent, provided that at least one of R¹ to R⁸ representsa substituted or unsubstituted carbazolyl group. Ar¹ to Ar³ eachindependently represent a substituted or unsubstituted aromatic ring ora heteroaromatic ring)[2] The compound according to [1], wherein in the general formula (201),at least one of R³ and R⁶ represents a substituted or unsubstitutedcarbazolyl group.[3] The compound according to [1] or [2], wherein the carbazolyl groupis a 1-carbazolyl group, a 2-carbazolyl group, a 3-carbazolyl group or a4-carbazolyl group.[4] The compound according to any one of [1] to [3], wherein thecarbazolyl group has a substituent on the nitrogen atom in the carbazolecyclic structure.[5] The compound according to any one of [1] to [4], wherein in thegeneral formula (201), at least one of Ar¹, Ar² and Ar³ represents abenzene ring or a naphthalene ring.[6] The compound according to any one of [1] to [5], wherein in thegeneral formula (201), Ar¹, Ar² and Ar³ each represent the same aromaticring or the same heteroaromatic ring.[7] The compound according to any one of [1] to [6], wherein in thegeneral formula (201), Ar¹, Ar² and Ar³ each represent a benzene ring.

Examples of the compound include the following compounds.

Examples of the preferred delayed fluorescent material include compoundsrepresented by the following general formulae. The entire description ofWO 2013/133359 including the paragraphs 0007 to 0032 and 0079 to 0084 isincorporated herein by reference as a part of the description of thepresent application.

[In the general formula (212), Ar¹, Ar², Ar³, Ar⁴, Ar⁵ and Ar⁶ eachindependently represent a substituted or unsubstituted aryl group.]

Specific examples of the compound represented by the general formula(212) include the compound represented by the following structuralformula.

Specific examples of the compound represented by the general formula(212) include the compounds shown in the following table. Here, Ar¹,Ar², Ar³, Ar⁴, Ar⁵ and Ar⁶ are the same as each other, and are expressedby Ar.

TABLE 21 Compound No. Ar 4002 4-fluorophenyl 4003 3-fluorophenyl 40042-fluorophenyl 4005 3,5-difluorophenyl 4006 2,4,6-trifluorophenyl 40074-methylphenyl 4008 3-methylphenyl 4009 2-methylphenyl 40103,5-dimethylphenyl 4011 2,4,6-trimethylphenyl 4012 4-ethylphenyl 40133-ethylphenyl 4014 2-ethylphenyl 4015 3,5-diethylphenyl 40164-propylphenyl 4017 3-propylphenyl 4018 3,5-dipropylphenyl 40194-tert-butylphenyl 4020 3-tert-butylphenyl 4021 3,5-di-tert-butylphenyl4022 1-naphthyl 4023 2-naphthyl

Examples of the preferred delayed fluorescent material include compoundsrepresented by the following general formula. The entire description ofWO 2013/161437 including the paragraphs 0008 to 0054 and 0101 to 0121 isincorporated herein by reference as a part of the description of thepresent application.

[In the general formula (221), R¹ to R¹⁰ each independently represent ahydrogen atom or a substituent, provided that at least one of R¹ to R¹⁰represents a substituted or unsubstituted aryl group, a substituted orunsubstituted diarylamino group or a substituted or unsubstituted9-carbazolyl group. R¹ and R², R² and R³, R³ and R⁴, R⁴ and R⁵, R⁵ andR⁶, R⁶ and R⁷, R⁷ and R⁸, R⁸ and R⁹, and R⁹ and R¹⁰ each may be bondedto each other to form a cyclic structure.]

Specific examples of the compound include the following compounds.

Examples of the preferred delayed fluorescent material include compoundsrepresented by the following general formula. The entire description ofJP-A-2014-9352 including the paragraphs 0007 to 0041 and 0060 to 0069 isincorporated herein by reference as a part of the description of thepresent application.

[In the general formula (231), R¹ to R⁴ each independently represent ahydrogen atom or a substituted or unsubstituted (N,N-diarylamino)arylgroup, provided that at least one of R¹ to R⁴ represents a substitutedor unsubstituted (N,N-diarylamino)aryl group. Two aryl groupsconstituting the diarylamino moiety of the (N,N-diarylamino)aryl groupmay be bonded to each other. W¹, W², X¹, X², Y¹, Y², Z¹ and Z² eachindependently represent a carbon atom or a nitrogen atom. m¹ to m⁴ eachindependently represent 0, 1 or 2.]

Examples of the compound include the following compounds.

Examples of the preferred delayed fluorescent material include compoundsrepresented by the following general formula. The entire description ofJP-A-2014-9224 including the paragraphs 0008 to 0048 and 0067 to 0076 isincorporated herein by reference as a part of the description of thepresent application.

[In the general formula (241), R¹ to R⁶ each independently represent ahydrogen atom or a substituent, provided that at least one of R¹ to R⁶represents a substituted or unsubstituted (N,N-diarylamino)aryl group,and two aryl groups constituting the diarylamino moiety of the(N,N-diarylamino)aryl group may be bonded to each other. X¹ to X and Y¹to Y⁶ each independently represent a carbon atom or a nitrogen atom. n¹,n², p¹, p², q¹ and q² each independently represent 0, 1 or 2.]

Examples of the compound include the following compounds.

Preferred compounds for host materials that can be used together withthe host material for delayed fluorescent materials of the presentinvention are mentioned below.

Preferred examples of compounds usable as a hole injection material arementioned below.

Next, preferred examples of compounds usable as a hole transportmaterial are mentioned below.

Next, preferred examples of compounds usable as a hole barrier materialare mentioned below.

Next, preferred examples of compounds usable as a hole barrier materialare mentioned below.

Next, preferred examples of compounds usable as a hole transportmaterial are mentioned below.

Next, preferred examples of compounds usable as an electron injectionmaterial are mentioned below.

Further, preferred examples of additive compounds are mentioned below.For example, the compounds may be added as a stabilization material.

The organic electroluminescence device thus produced by theaforementioned method emits light on application of an electric fieldbetween the anode and the cathode of the device. In this case, when thelight emission is caused by the excited singlet energy, light having awavelength that corresponds to the energy level thereof may be confirmedas fluorescent light and delayed fluorescent light. When the lightemission is caused by the excited triplet energy, light having awavelength that corresponds to the energy level thereof may be confirmedas phosphorescent light. The normal fluorescent light has a shorterlight emission lifetime than the delayed fluorescent light, and thus thelight emission lifetime may be distinguished between the fluorescentlight and the delayed fluorescent light.

On the other hand, the phosphorescent light could not be substantiallyobserved with a normal organic compound, such as the compound of theinvention, at room temperature since the excited triplet energy isconverted to heat or the like due to the instability thereof, and isimmediately deactivated with a short lifetime. The excited tripletenergy of the normal organic compound may be measured by observing lightemission under an extremely low temperature condition.

The organic electroluminescence device of the invention may be appliedto any of a single device, a structure with plural devices disposed inan array, and a structure having anodes and cathodes disposed in an X-Ymatrix. According to the invention, an organic light-emitting devicethat is largely improved in light emission efficiency may be obtained byadding the compound represented by the general formula (1) to thelight-emitting layer. The organic light-emitting device, such as theorganic electroluminescence device, of the invention may be applied to afurther wide range of purposes. For example, an organicelectroluminescent display apparatus may be produced with the organicelectroluminescence device of the invention, and for the detailsthereof, reference may be made to Seiji Tokito, Chihaya Adachi andHideyuki Murata, “Yuki EL Display” (Organic EL Display) (Ohm-sha, Ltd.).In particular, the organic electroluminescence device of the inventionmay be applied to organic electroluminescent illumination and backlightwhich are highly demanded.

EXAMPLES

The features of the invention will be described more specifically withreference to Synthesis Examples and Examples below. The materials,processes, procedures and the like shown below may be appropriatelymodified unless they deviate from the substance of the invention.Accordingly, the scope of the invention is not construed as beinglimited to the specific examples shown below. The light emissioncharacteristics were evaluated by using a source meter (2400 Series,produced by Keithley Instruments Inc.), a semiconductor parameteranalyzer (E5273A, produced by Agilent Technologies, Inc.), an opticalpower meter (1930C, produced by Newport Corporation), an opticalspectrometer (USB2000, produced by Ocean Optics, Inc.), aspectroradiometer (SR-3, produced by Topcon Corporation), and a streakcamera (Model C4334, produced by Hamamatsu Photonics K.K.).

(Synthesis Example 1) Synthesis of Compound 4

A commercial product, 3,5-dibromotoluene (2.50 g, 10 mmol) was dissolvedin 80 ml of dimethylformamide, tripotassium phosphate (12.74 g, 60mmol), PdCl₂(PPh₃)₂ (dichlorobis(triphenylphosphine) palladium(II): 0.35g, 0.5 mmol) and triphenylenyl boronate (5.44 g, 20 mmol) were added,and stirred at room temperature for 24 hours, and then reacted at 60° C.for 24 hours. The reaction solution was left cooled, 100 ml of water wasadded, filtered, washed with 50 ml of acetone, and further washed with80 ml of water and 80 ml of methanol to give the compound 4 with a yieldof 4.90 g, 90%. The reaction product was purified by reduced-pressuresublimation. MS (70 eV, EI) m/z=544 (M⁺).

(Synthesis Example 2) Synthesis of Compound 9

A commercial product, 3,3′,5,5′-tetrabromobiphenyl (1.41 g, 3 mmol) wasdissolved in 120 ml of dimethylformamide, tripotassium phosphate (7.64g, 36 mmol), PdCl₂(PPh₃)₂ (0.11 g, 0.2 mmol) and triphenylenyl boronate(3.27 g, 12 mmol) were added, and stirred at room temperature for 24hours, and then reacted at 80° C. for 24 hours. The reaction solutionwas left cooled, 240 ml of water was added, filtered, washed with 200 mlof acetone, and further washed with 100 ml of water and 200 ml ofmethanol to give the compound 9 with a yield, 2.45 g, 77%. The reactionproduct was purified by reduced-pressure sublimation.

MS (MALDI) m/z=1059 (M+1).

(Synthesis Example 3) Synthesis of Compound 10

A commercial product, Br-triphenylene (3.07 g, 10 mmol) was dissolved in80 ml of dewatered tetrahydrofuran in a nitrogen stream atmosphere, andkept at an internal temperature of −85° C. in an ethanol bath withliquid nitrogen. A hexane solution of n-butyl lithium (7.5 ml, 12 mmol)was gradually added to the solution, while kept at an internaltemperature of −80° C. or lower. After 1 hour, a solution prepared bydissolving methyl chloroformate (1.42 g, 15 mmol) in 20 ml of dewateredtetrahydrofuran was added while kept at an internal temperature of −80°C. or lower, then kept at −85° C. for 1 hour, and thereafter stirredovernight at room temperature. 100 ml of water was gradually added tothe reaction solution, filtered, and then washed with methanol and waterto give the compound 10 with a yield of 1.21 g, 42%. The reactionproduct was purified by reduced-pressure sublimation.

MS (70 eV, EI) m/z=482 (M+).

(Example 1) Production and Evaluation of Organic ElectroluminescenceDevice Using Compound 1

On a glass substrate with an anode of indium-tin oxide (ITO) formedthereon to have a thickness of 100 nm, each thin film was laminatedaccording to a vacuum evaporation method at a vacuum degree of 5.0×10⁻⁴Pa. First, HAT-CN was formed on ITO in a thickness of 10 nm, and thenTris-PCZ was formed thereon in a thickness of 30 nm. Next, a layerhaving a thickness of 30 nm was formed through co-evaporation with HK13and the compound 1 from different evaporation sources, thereby forming alight-emitting layer. At this time, the concentration of HK13 was 6.0%by weight. Next, T2T was formed in a thickness of 10 nm, Bpy-TP2 wasformed in a thickness of 40 nm, and further lithium fluoride (LiF) wasdeposited through vacuum evaporation in a thickness of 0.8 nm, andthereafter aluminum (Al) was deposited in a thickness of 100 nm, therebyforming a cathode to provide an organic electroluminescence device. Thelifetime characteristic of the produced organic electroluminescencedevice, as measured at an initial brightness of 1000 Cd/m² and at acurrent density of 54.5 mA/cm², is shown in FIG. 2.

(Comparative Example 1) Production and Evaluation of OrganicElectroluminescence Device Using Comparative Compound A (CBP)

An organic electroluminescence device was produced in the same manner asin Example 1 except that CBP was used to form a light-emitting layer inplace of the compound 1. The lifetime characteristic of the producedorganic electroluminescence device, as measured at an initial brightnessof 1000 Cd/m² and at a current density of 54.5 mA/cm², is shown in FIG.2.

The LT50 lifetime of the organic electroluminescence device using thecomparative compound A was 12 days, but the LT50 lifetime of the organicelectroluminescence device using the compound 1 was 277 days, that is,the latter device had a far longer lifetime.

(Example 2) Production and Evaluation of Organic ElectroluminescenceDevice Using Composite Host Material of Compound 10 and CBP

An organic electroluminescence device was produced in the same manner asin Example 1 except that a light-emitting layer having a thickness of 30nm was formed through co-deposition with HK13, the compound 10 and CBPfrom different evaporation sources, and the concentration of HK13 in thelight-emitting layer was 1% by weight.

The voltage-current density characteristic of the produced organicelectroluminescent device is shown in FIG. 3, the currentdensity-external quantum efficiency characteristic thereof is in FIG. 4,the lifetime characteristic thereof is in FIG. 5, and the characteristicvalues thereof measured at 1000 Cd/m² are shown in Table 22.

(Comparative Example 2) Production and Evaluation of OrganicElectroluminescence Device Using Comparative Compound A (CBP)

An organic electroluminescence device was produced in the same manner asin Example 1 except that CBP was used in place of the compound 1 to forma light-emitting layer and the concentration of HK13 in thelight-emitting layer was 1% by weight.

The voltage-current density characteristic of the produced organicelectroluminescent device is shown in FIG. 3, the currentdensity-external quantum efficiency characteristic thereof is in FIG. 4,the lifetime characteristic thereof is in FIG. 5, and the characteristicvalues thereof measured at 1000 Cd/m² are shown in Table 22.

(Comparative Example 3) Production and Evaluation of OrganicElectroluminescence Device Using Composite Host Material of ComparativeCompound B and CBP

An organic electroluminescence device was produced in the same manner asin Example 1 except that a light-emitting layer having a thickness of 30nm was formed through co-deposition with HK13, the comparative compoundB and CBP from different evaporation sources, and the concentration ofHK13 in the light-emitting layer was 1% by weight.

The voltage-current density characteristic of the produced organicelectroluminescent device is shown in FIG. 3, the currentdensity-external quantum efficiency characteristic thereof is in FIG. 4,and the characteristic values thereof measured at 1000 Cd/m² are shownin Table 22. The lifetime characteristic of the device was measured inthe same manner as in Example 2, and LT50 thereof was 585 hours.

(Example 3) Production and Evaluation of Organic ElectroluminescenceDevice Using Different Light-Emitting Material and Composite HostMaterial of Compound 10 and CBP

An organic electroluminescence device was produced in the same manner asin Example 2 except that YH016 was used in place of HK13.

The characteristic values of the produced organic electroluminescencedevice, as measured at 1000 Cd/m², are shown in Table 22.

TABLE 22 External Maximum Quantum Current Drive Current Power EmissionLT50 Light-Emitting Efficiency Density Voltage Efficiency EfficiencyWavelength Lifetime Host Material Material (%) (mA/cm²) (V) (Cd/A)(lm/W) CIE (x, y) (nm) (H) ΔV Example 2 50% CBP:50% 1% HK13 3.4 15.2 5.66.7 3.8 0.55, 0.44 598 1050 — compound 10 Comparative CBP 1% HK13 1.629.6 8.5 3.3 1.3 0.53, 0.44 593 48 1.4 Example 2 Comparative 50% CBP:50%1% HK13 2.2 24.1 7.2 4.1 1.8 0.55, 0.44 599 585 0.84 Example 3comparative compound B Example 3 50% CBP:50% 1% YH016 4.5 14.3 5.3 7.04.2 0.58, 0.42 616 1550 — compound 10

The organic electroluminescence device using a composite host materialof the compound 10 and CBP has a remarkably longer LT50 lifetime, ascompared with the organic electroluminescence device using thecomparative compound A (CBP) and the organic electroluminescence deviceusing a composite host material of the comparative compound B and CBP,and can operate at a low drive voltage, and the current efficiency, thepower efficiency and the external quantum yield thereof are all highvalues.

INDUSTRIAL APPLICABILITY

The compound of the invention is useful as a host material for delayedfluorescent materials. Accordingly, the compound of the invention may beeffectively used as a host material for delayed fluorescent materialsfor organic light-emitting devices such as organic electroluminescencedevices, etc. By using the host material for delayed fluorescentmaterials of the present invention, it is possible to provide an organiclight-emitting device having a high efficiency, capable of operating ata low drive voltage and having a long lifetime. Thus, the invention hashigh industrial applicability.

REFERENCE SIGNS LIST

-   1 Substrate-   2 Anode-   3 Hole Injection Layer-   4 Hole Transport Layer-   5 Light-Emitting Layer-   6 Electron Transport Layer-   7 Cathode

1. (canceled)
 2. The organic light-emitting device according to claim13, wherein Z is a substituted or unsubstituted, n-valent aromatichydrocarbon group.
 3. The organic light-emitting device according toclaim 2, wherein Z is an n-valent benzene residue.
 4. The organiclight-emitting device according to claim 3, wherein Tr bonds to the1-position and the 3-position of the benzene residue.
 5. The organiclight-emitting device according to claim 2, wherein Z is an n-valentbiphenyl residue.
 6. The organic light-emitting device according toclaim 2, wherein Z is an n-valent aromatic hydrocarbon group substitutedwith a substituted or unsubstituted alkyl group or a substituted orunsubstituted aryl group.
 7. The organic light-emitting device accordingto claim 13, wherein Z is a carbonyl group.
 8. The organiclight-emitting device according to claim 7, wherein at least one Tr hasa substituent represented by the following general formula (2):Tr⁴-CO—  General Formula (2) wherein Tr⁴ represents a substituted orunsubstituted triphenylenyl group.
 9. The organic light-emitting deviceaccording to claim 8, wherein two Tr's have, in total, 1 to 5substituents each represented by the general formula (2).
 10. Theorganic light-emitting device according to claim 7, which contains apartial structure with a carbonyl group bonding to the 2-position, the3-position, the 6-position, the 7-position, the 10-position or the11-position of the triphenylene ring inside the molecule.
 11. Theorganic light-emitting device according to claim 10, wherein all thecarbonyl groups bonding to the triphenylene ring existing inside themolecule bond to the 2-position, the 3-position, the 6-position, the7-position, the 10-position or the 11-position of the triphenylene ring.12. The organic light-emitting device according to claim 13, wherein atleast one Tr in the general formula (1) is a triphenylenyl groupsubstituted with a substituted or unsubstituted alkyl group or asubstituted or unsubstituted aryl group.
 13. An organic light-emittingdevice comprising a layer that contains a delayed fluorescent materialand a host material represented by the following general formula (1):(Tr)_(n)-Z  General Formula (1) wherein Tr represents a substituted orunsubstituted triphenylenyl group, and plural Tr's existing in thegeneral formula (1) may be the same as or different from each other; Zrepresents a carbonyl group or a substituted or unsubstituted, n-valentaromatic hydrocarbon group; n represents an integer of 2 to 6, but whenZ is a carbonyl group, then n is
 2. 14. (canceled)
 15. The organiclight-emitting device according to claim 13, which is an organicelectroluminescence device.
 16. A compound represented by the followinggeneral formula (3):Tr¹-CO-Tr²  General Formula (3) wherein Tr¹ and Tr² each independentlyrepresent a substituted or unsubstituted triphenylenyl group, and Tr¹and Tr² may be the same as or different from each other.
 17. A compoundrepresented by the following general formula (4):(Tr³)_(n1)-Z  General Formula (4) wherein Tr³ represents a substitutedor unsubstituted triphenylenyl group, and plural Tr³'s existing in thegeneral formula (4) may be the same as or different from each other; Z¹represents a substituted or unsubstituted n-valent aromatic hydrocarbongroup; n1 represents an integer of 2 to 6; at least one of Tr³ and Z¹ issubstituted with a substituted or unsubstituted alkyl group or asubstituted or unsubstituted aryl group; when Tr³ is unsubstituted, thenZ¹ is a benzene ring residue substituted with a phenyl group or a methylgroup and bonds to Tr³ at the 1-position and the 3-position, or is abiphenyl residue substituted with a phenyl group.